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image of Synthesis of Biologically Active Five-Member Nitrogenated Heterocycles Under Microwave Irradiation

Abstract

Microwaves have become a fundamental tool for the synthesis of many heterocyclic compounds, enabling more environmentally friendly protocols and faster, more efficient synthesis processes with better product yields and selectivity. In this work, we review the most recent advances in the use of microwaves as an efficient tool for the synthesis of biologically active five-membered nitrogenated heterocycles, focusing on pyrroles, pyrazoles, imidazoles, indoles, benzimidazoles, and benzotriazoles, as well as their derivatives, which have shown remarkable biological activity. Across all results shown, the use of microwave dielectric heating demonstrates marked advantages in synthetic procedures compared to conventional methods.

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2026-04-30
2026-05-19
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References

  1. Hoz A. Díaz-Ortiz A. Moreno A. Sanchéz-Migallón A. Prieto P. Carrillo J. Vázquez E. Gómez M. Herrero M. Microwave-assisted reactions in heterocyclic compounds with applications in medicinal and supramolecular chemistry. Comb. Chem. High Throughput Screen. 2007 10 10 877 902 10.2174/138620707783220347 18288949
    [Google Scholar]
  2. Tiwari G. Khanna A. Mishra V.K. Sagar R. Recent developments on microwave-assisted organic synthesis of nitrogen- and oxygen-containing preferred heterocyclic scaffolds. RSC Advances 2023 13 47 32858 32892 10.1039/D3RA05986C 37942237
    [Google Scholar]
  3. Banerjee S. Periyasamy S. Muthukumaradoss K. Deivasigamani P. Saravanan V. Revolutionizing organic synthesis through green chemistry: metal-free, bio-based, and microwave-assisted methods. Front Chem. 2025 13 1656935 10.3389/fchem.2025.1656935 40832566
    [Google Scholar]
  4. Martina K. Cravotto G. Varma R.S. Impact of microwaves on organic synthesis and strategies toward flow processes and scaling up. J. Org. Chem. 2021 86 20 13857 13872 10.1021/acs.joc.1c00865 34125541
    [Google Scholar]
  5. Dallinger D. Kappe C.O. Microwave-assisted synthesis in water as solvent. Chem. Rev. 2007 107 6 2563 2591 10.1021/cr0509410 17451275
    [Google Scholar]
  6. Oliver Kappe C. Microwave dielectric heating in synthetic organic chemistry. Chem. Soc. Rev. 2008 37 6 1127 1139 10.1039/b803001b 18497926
    [Google Scholar]
  7. Pibiri I. Recent advances: Heterocycles in drugs and drug discovery. Int. J. Mol. Sci. 2024 25 17 9503 10.3390/ijms25179503 39273451
    [Google Scholar]
  8. Han B. He X.H. Liu Y.Q. He G. Peng C. Li J.L. Asymmetric organocatalysis: An enabling technology for medicinal chemistry. Chem. Soc. Rev. 2021 50 3 1522 1586 10.1039/D0CS00196A 33496291
    [Google Scholar]
  9. Ebenezer O. Jordaan M.A. Carena G. Bono T. Shapi M. Tuszynski J.A. An overview of the biological evaluation of selected nitrogen-containing heterocycle medicinal chemistry compounds. Int. J. Mol. Sci. 2022 23 15 8117 10.3390/ijms23158117 35897691
    [Google Scholar]
  10. Vitaku E. Smith D.T. Njardarson J.T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J. Med. Chem. 2014 57 24 10257 10274 10.1021/jm501100b 25255204
    [Google Scholar]
  11. Amin A. Qadir T. Sharma P. K. Jeelani I. Abe H. A review on the medicinal and industrial applications of N-containing heterocycles. The Open Med. Chem. J. 2022 19 10.2174/18741045‑v16‑e2209010
    [Google Scholar]
  12. Luo W. Liu Y. Qin H. Zhao Z. Wang S. He W. Tang S. Peng J. Nitrogen-containing heterocyclic drug products approved by the FDA in 2023: Synthesis and biological activity. Eur. J. Med. Chem. 2024 279 116838 10.1016/j.ejmech.2024.116838 39255645
    [Google Scholar]
  13. Joshi S.D. Vagdevi H.M. Vaidya V.P. Gadaginamath G.S. Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial and antitubercular agents. Eur. J. Med. Chem. 2008 43 9 1989 1996 10.1016/j.ejmech.2007.11.016 18207286
    [Google Scholar]
  14. Bouchal B. Abrigach F. Takfaoui A. Elidrissi Errahhali M. Elidrissi Errahhali M. Dixneuf P.H. Doucet H. Touzani R. Bellaoui M. Identification of novel antifungal agents: antimicrobial evaluation, SAR, ADME–Tox and molecular docking studies of a series of imidazole derivatives. BMC Chem. 2019 13 1 100 10.1186/s13065‑019‑0623‑6 31410411
    [Google Scholar]
  15. Ewies F. El-Hussieny E. Synthesis and utilization of tetrahydronaphthalene-1,3-dicarbonitrile as a source of benzo[f]quinazoline, pyridine, imidazole derivatives with antitumor activity and molecular docking and dynamics studies. Heterocycles 2022 104 11 1935 10.3987/COM‑22‑14708
    [Google Scholar]
  16. Kumar A. Kaushal A. Verma P.K. Gupta M.K. Chandra G. Kumar U. Yadav A.K. Kumar D. An insight into recent developments in imidazole based heterocyclic compounds as anticancer agents: Synthesis, SARs, and mechanism of actions. Eur. J. Med. Chem. 2024 280 116896 10.1016/j.ejmech.2024.116896 39366252
    [Google Scholar]
  17. Galenko-Yaroshevsky P.A. Shelemekh O.V. Popkov V.L. Zadorozhniy A.V. Nektarevskaya I.B. Bunyatyan N.D. Murashko R.A. Lebedeva S.A. Zelenskaya A.V. Uvarov A.V. Gulevskaya O.N. Alukhanyan L.O. Glechyan T.R. Sergeeva A.V. Kornetskaya A.V. Korovaykin N.E. Study of the anti-inflammatory, analgesic, ulcerogenic and anti-ulcerogenic activity of N-isopropenylimidazole zinc complex derivative. Res. Result. Pharmacol. 2024 10 1 23 43 10.18413/rrpharmacology.10.443
    [Google Scholar]
  18. Dinodia M. Recent advances in N-heterocycles for COVID-19 treatment: A mini review. Med. Chem. 2023 19 8 717 729 10.2174/1573406419666230228115410 36852805
    [Google Scholar]
  19. Kumari S. Maddeboina K. Bachu R.D. Boddu S.H.S. Trippier P.C. Tiwari A.K. Pivotal role of nitrogen heterocycles in Alzheimer’s disease drug discovery. Drug Discov. Today 2022 27 10 103322 10.1016/j.drudis.2022.07.007 35868626
    [Google Scholar]
  20. Obaid R.J. Mughal E.U. Naeem N. Al-Rooqi M.M. Sadiq A. Jassas R.S. Moussa Z. Ahmed S.A. Pharmacological significance of nitrogen-containing five and six-membered heterocyclic scaffolds as potent cholinesterase inhibitors for drug discovery. Process Biochem. 2022 120 250 259 10.1016/j.procbio.2022.06.009
    [Google Scholar]
  21. Lakshmidevi V.R. Reeja D. Rajan A.R. Vinod B. Advanced spectrum of imidazole derivatives in therapeutics: A review. J. Chem. Rev. 2023 5 3 241 262 10.22034/jcr.2023.385802.1215
    [Google Scholar]
  22. Canh Pham E. Truong T.N. Design, microwave-assisted synthesis, antimicrobial and anticancer evaluation, and in silico studies of some 2-naphthamide derivatives as DHFR and VEGFR-2 inhibitors. ACS Omega 2022 7 37 33614 33628 10.1021/acsomega.2c05206 36157776
    [Google Scholar]
  23. Vani I. Sireesha R. Mak K.K. Mallikarjuna Rao P. Prasad K.R.S. Basaveswara Rao M.V. Microwave assisted synthesis and antimicrobial and antioxidant activities of dimers of 1,2,3-triazole-benzofuran bearing alkyl spacer derivatives. Chemical Data Collections 2021 31 100605 10.1016/j.cdc.2020.100605
    [Google Scholar]
  24. Dauletbakov A. Belyankova Y. Assylbekova S. Zolotareva D. Bayazit S. Baktybayeva L. Kemelbekov U. Yu V. Ibragimova N. Zazybin A. Ultrasound and microwave-assisted synthesis and antidiabetic and hematopoietic activity of diphenhydramine derivatives. Molecules 2025 30 14 2967 10.3390/molecules30142967 40733233
    [Google Scholar]
  25. Vachhani M. Lalpara J. Hadiyal S. Microwave-assisted synthesis of bioactive tetrahydropyrimidine derivatives as antidiabetic agents. Folia Medica 2022 64 3 478 10.3897/folmed.64.e62476
    [Google Scholar]
  26. Amira A. K’tir H. Aouf Z. Khaldi T. Bentoumi H. Khattabi L. Zerrouki R. Ibrahim-Ouali M. Aouf N.E. One‐pot microwave‐assisted synthesis, in vitro anti‐inflammatory evaluation and computer‐aided molecular design of novel sulfamide‐containing bisphosphonates derivatives. ChemistrySelect 2022 7 28 e202201889 10.1002/slct.202201889
    [Google Scholar]
  27. Roth B.D. The discovery and development of atorvastatin, a potent novel hypolipidemic agent. Prog. Med. Chem. 2002 40 1 22 10.1016/S0079‑6468(08)70080‑8 12516521
    [Google Scholar]
  28. Asif M. A mini review: Biological significances of nitrogen hetero atom containing heterocyclic compounds. Int. J. Bioorg. Chem. 2017 2 3 146 152 10.11648/j.ijbc.20170203.20
    [Google Scholar]
  29. Heravi M.M. Zadsirjan V. Prescribed drugs containing nitrogen heterocycles: an overview. RSC Advances 2020 10 72 44247 44311 10.1039/D0RA09198G 35557843
    [Google Scholar]
  30. Tolomeu H.V. Fraga C.A.M. Imidazole: Synthesis, Functionalization and Physicochemical Properties of a Privileged Structure in Medicinal Chemistry. Molecules 2023 28 2 838 10.3390/molecules28020838 36677894
    [Google Scholar]
  31. Alam M.A. Pyrazole: An emerging privileged scaffold in drug discovery. Future Med. Chem. 2023 15 21 2011 2023 10.4155/fmc‑2023‑0207 37933613
    [Google Scholar]
  32. Baumann M. Baxendale I.R. Ley S.V. Nikbin N. An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals. Beilstein J. Org. Chem. 2011 7 442 495 10.3762/bjoc.7.57 21647262
    [Google Scholar]
  33. Adhikari A. Bhakta S. Ghosh T. Microwave-assisted synthesis of bioactive heterocycles: An overview. Tetrahedron 2022 126 133085 10.1016/j.tet.2022.133085
    [Google Scholar]
  34. Garella D. Borretto E. Di Stilo A. Martina K. Cravotto G. Cintas P. Microwave-assisted synthesis of N-heterocycles in medicinal chemistry. MedChemComm 2013 4 10 1323 1343 10.1039/c3md00152k
    [Google Scholar]
  35. Almas I. Malik A. Rasool N. Kanwal A. Khalid T. Nawaz H. Microwave-assisted protocol towards synthesis of heterocyclic molecules: A Comparative analysis with conventional synthetic methodologies (Years 2019–2023): A Review. Mol. Divers. 2024 29 2717 10.1007/s11030‑024‑10981‑y 39302538
    [Google Scholar]
  36. Meera G. Rohit K.R. Saranya S. Anilkumar G. Microwave assisted synthesis of five membered nitrogen heterocycles. RSC Advances 2020 10 59 36031 36041 10.1039/D0RA05150K 35517065
    [Google Scholar]
  37. Bandyopadhyay D. Banik B.K. Synthesis of Medicinally privileged heterocycles through dielectric heating. Curr. Med. Chem. 2018 24 41 4596 4626 10.2174/0929867324666170223152137 28240166
    [Google Scholar]
  38. Santagada V. Frecentese F. Perissutti E. Fiorino F. Severino B. Caliendo G. Microwave assisted synthesis: A new technology in drug discovery. Mini Rev. Med. Chem. 2009 9 3 340 358 10.2174/1389557510909030340 19275727
    [Google Scholar]
  39. Starosotnikov A.M. Bastrakov M.A. Dalinger I.L. Recent Developments in the Synthesis and Functionalization of Nitrogen Heterocycles. MDPI - Multidisciplinary Digital Publishing Institute 2024 10.3390/books978‑3‑7258‑2080‑1
    [Google Scholar]
  40. Bianco M.C.A.D. Marinho D.I.L.F. Hoelz L.V.B. Bastos M.M. Boechat N. Pyrroles as privileged scaffolds in the search for new potential HIV inhibitors. Pharmaceuticals 2021 14 9 893 10.3390/ph14090893 34577593
    [Google Scholar]
  41. Wójcicka A. Redzicka A. An overview of the biological activity of pyrrolo[3,4-c]pyridine derivatives. Pharmaceuticals 2021 14 4 354 10.3390/ph14040354 33920479
    [Google Scholar]
  42. Alghamdi S.S. Suliman R.S. Almutairi K. Kahtani K. Aljatli D. Imidazole as a promising medicinal scaffold: Current status and future direction. Drug Des. Devel. Ther. 2021 15 3289 3312 10.2147/DDDT.S307113 34354342
    [Google Scholar]
  43. Serdaliyeva D. Nurgozhin T. Satbayeva E. Khayitova M. Seitaliyeva A. Ananyeva L. Review of pharmacological effects of imidazole derivatives. J. Clin. Med. Kazakhstan 2022 19 3 11 15 10.23950/jcmk/12117
    [Google Scholar]
  44. Li G. Cheng Y. Han C. Song C. Huang N. Du Y. Pyrazole-containing pharmaceuticals: target, pharmacological activity, and their SAR studies. RSC Med. Chem. 2022 13 11 1300 1321 10.1039/D2MD00206J 36439976
    [Google Scholar]
  45. Singh S. Singh K. Tahlan S. A comprehensive review on synthetic strategy and MOA of marketed drugs having therapeutically potential chemical entity pyrazole. J. Indian Chem. Soc. 2024 21 10 2531 2564 10.1007/s13738‑024‑03095‑7
    [Google Scholar]
  46. Zeng W. Han C. Mohammed S. Li S. Song Y. Sun F. Du Y. Indole-containing pharmaceuticals: targets, pharmacological activities, and SAR studies. RSC Med. Chem. 2024 15 3 788 808 10.1039/D3MD00677H 38516587
    [Google Scholar]
  47. Murtazaeva Z. Nasrullaev A. Buronov A. Gaybullaev S. Nie L. Numonov S. Khushnazarov Z. Turgunov D. Kuryazov R. Zhao J. Bozorov K. Imidazole hybrids: A Privileged class of heterocycles in medicinal chemistry with new insights into anticancer activity. Molecules 2025 30 10 2245 10.3390/molecules30102245 40430417
    [Google Scholar]
  48. Briguglio I. Piras S. Corona P. Gavini E. Nieddu M. Boatto G. Carta A. Benzotriazole: An overview on its versatile biological behavior. Eur. J. Med. Chem. 2015 97 612 648 10.1016/j.ejmech.2014.09.089 25293580
    [Google Scholar]
  49. Abubakar Dahiru Ritu Sharma Ajmand Safiya Soniya Sawashi Abubakar Muhd Shafi’I Advancements in benzotriazole derivatives: from synthesis to pharmacological applications. GSC Biol. Pharm. Sci. 2024 29 2 271 285 10.30574/gscbps.2024.29.2.0384
    [Google Scholar]
  50. Knorr L. Einwirkung von acetessigester auf phenylhydrazin. Ber. Dtsch. Chem. Ges. 1883 16 2 2597 2599 10.1002/cber.188301602194
    [Google Scholar]
  51. Karrouchi K. Radi S. Ramli Y. Taoufik J. Mabkhot Y.N. Al-aizari F.A. Ansar M. Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review. Molecules 2018 23 1 134 10.3390/molecules23010134 29329257
    [Google Scholar]
  52. Kabi A.K. Sravani S. Gujjarappa R. Garg A. Vodnala N. Tyagi U. Kaldhi D. Singh V. Gupta S. Malakar C.C. Overview on biological activities of pyrazole derivatives. Nanostructured Biomaterials: Basic Structures and Applications. Swain B.P. Singapore Springer 2022 229 306 10.1007/978‑981‑16‑8399‑2_7
    [Google Scholar]
  53. Ebenezer O. Shapi M. Tuszynski J.A. A Review of the Recent Development in the Synthesis and Biological Evaluations of Pyrazole Derivatives. Biomedicines 2022 10 5 1124 10.3390/biomedicines10051124 35625859
    [Google Scholar]
  54. Bennani F.E. Doudach L. Cherrah Y. Ramli Y. Karrouchi K. Ansar M. Faouzi M.E.A. Overview of recent developments of pyrazole derivatives as an anticancer agent in different cell line. Bioorg. Chem. 2020 97 103470 10.1016/j.bioorg.2019.103470 32120072
    [Google Scholar]
  55. Silva V.L.M. Elguero J. Silva A.M.S. Current progress on antioxidants incorporating the pyrazole core. Eur. J. Med. Chem. 2018 156 394 429 10.1016/j.ejmech.2018.07.007 30015075
    [Google Scholar]
  56. Kumar H. Saini D. Jain S. Jain N. Pyrazole scaffold: A remarkable tool in the development of anticancer agents. Eur. J. Med. Chem. 2013 70 248 258 10.1016/j.ejmech.2013.10.004 24161702
    [Google Scholar]
  57. Küçükgüzel Ş.G. Şenkardeş S. Recent advances in bioactive pyrazoles. Eur. J. Med. Chem. 2015 97 786 815 10.1016/j.ejmech.2014.11.059 25555743
    [Google Scholar]
  58. Mermer A. Keles T. Sirin Y. Recent studies of nitrogen containing heterocyclic compounds as novel antiviral agents: A review. Bioorg. Chem. 2021 114 105076 10.1016/j.bioorg.2021.105076 34157555
    [Google Scholar]
  59. Fustero S. Sánchez-Roselló M. Barrio P. Simón-Fuentes A. From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles. Chem. Rev. 2011 111 11 6984 7034 10.1021/cr2000459 21806021
    [Google Scholar]
  60. Leadbeater N.E. Microwave Heating as a Tool for Sustainable Chemistry. Boca Raton CRC Press 2010 10.1201/9781439812709
    [Google Scholar]
  61. Ju Y. Varma R.S. Aqueous N-heterocyclization of primary amines and hydrazines with dihalides: microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazine derivatives. J. Org. Chem. 2006 71 1 135 141 10.1021/jo051878h 16388628
    [Google Scholar]
  62. Humphries P.S. Finefield J.M. Microwave-assisted synthesis utilizing supported reagents: a rapid and versatile synthesis of 1,5-diarylpyrazoles. Tetrahedron Lett. 2006 47 14 2443 2446 10.1016/j.tetlet.2006.01.100
    [Google Scholar]
  63. Corradi A. Leonelli C. Rizzuti A. Rosa R. Veronesi P. Grandi R. Baldassari S. Villa C. New “green” approaches to the synthesis of pyrazole derivatives. Molecules 2007 12 7 1482 1495 10.3390/12071482 17909503
    [Google Scholar]
  64. Du K. Xia C. Wei M. Chen X. Zhang P. Microwave-assisted rapid synthesis of sugar-based pyrazole derivatives with anticancer activity in water. RSC Advances 2016 6 71 66803 66806 10.1039/C6RA05284C
    [Google Scholar]
  65. Selvam T.P. Kumar P.V. Saravanan G. Prakash C.R. Microwave-assisted synthesis, characterization and biological activity of novel pyrazole derivatives. J. Saudi Chem. Soc. 2014 18 6 1015 1021 10.1016/j.jscs.2011.12.006
    [Google Scholar]
  66. Kendre B.V. Landge M.G. Jadhav W.N. Bhusare S.R. Synthesis and bioactivities of some new 1H-pyrazole derivatives containing an aryl sulfonate moiety. Chin. Chem. Lett. 2013 24 4 325 328 10.1016/j.cclet.2013.02.016
    [Google Scholar]
  67. Kendre B.V. Landge M.G. Bhusare S.R. Synthesis and biological evaluation of some novel pyrazole, isoxazole, benzoxazepine, benzothiazepine and benzodiazepine derivatives bearing an aryl sulfonate moiety as antimicrobial and anti-inflammatory agents. Arab. J. Chem. 2019 12 8 2091 2097 10.1016/j.arabjc.2015.01.007
    [Google Scholar]
  68. Alshareef H.F. Mohamed H.A.E.H. Salaheldin A.M. Synthesis and Biological Evaluation of New Tacrine Analogues under Microwave Irradiation. Chem. Pharm. Bull. (Tokyo) 2017 65 8 732 738 10.1248/cpb.c17‑00113 28768927
    [Google Scholar]
  69. Mótyán G. Gopisetty M.K. Kiss-Faludy R.E. Kulmány Á. Zupkó I. Frank É. Kiricsi M. Anti-Cancer Activity of Novel Dihydrotestosterone-Derived Ring A-Condensed Pyrazoles on Androgen Non-Responsive Prostate Cancer Cell Lines. Int. J. Mol. Sci. 2019 20 9 2170 10.3390/ijms20092170 31052484
    [Google Scholar]
  70. Desai N.C. Bhatt K. Monapara J. Pandit U. Khedkar V.M. Conventional and Microwave-Assisted Synthesis, Antitubercular Activity, and Molecular Docking Studies of Pyrazole and Oxadiazole Hybrids. ACS Omega 2021 6 42 28270 28284 10.1021/acsomega.1c04411 34723024
    [Google Scholar]
  71. Runge F.F. Ueber einige Produkte der Steinkohlendestillation. Ann. Phys. 1834 107 5 65 78 10.1002/andp.18341070502
    [Google Scholar]
  72. Heilman D. Woski S. Voet D. Fundamentals of Biochemistry. 6th Ed Wiley 2024
    [Google Scholar]
  73. Bhardwaj V. Gumber D. Abbot V. Dhiman S. Sharma P. Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics. RSC Advances 2015 5 20 15233 15266 10.1039/C4RA15710A
    [Google Scholar]
  74. Gholap S.S. Pyrrole: An emerging scaffold for construction of valuable therapeutic agents. Eur. J. Med. Chem. 2016 110 13 31 10.1016/j.ejmech.2015.12.017 26807541
    [Google Scholar]
  75. Jeelan Basha N. Basavarajaiah S.M. Shyamsunder K. Therapeutic potential of pyrrole and pyrrolidine analogs: an update. Mol. Divers. 2022 26 5 2915 2937 10.1007/s11030‑022‑10387‑8 35079946
    [Google Scholar]
  76. Rusu A. Oancea O.L. Tanase C. Uncu L. Unlocking the potential of pyrrole: Recent advances in new pyrrole-containing compounds with antibacterial potential. Int. J. Mol. Sci. 2024 25 23 12873 10.3390/ijms252312873 39684580
    [Google Scholar]
  77. Manya B.S. Kumar M.R.P. Rajagopal K. Hassan M.A. Rab S.O. Alshehri M.A. Emran T.B. Insights into the biological activities and substituent effects of pyrrole derivatives: The chemistry‐biology connection. Chem. Biodivers. 2024 21 8 e202400534 10.1002/cbdv.202400534 38771305
    [Google Scholar]
  78. Ahmad S. Alam O. Naim M.J. Shaquiquzzaman M. Alam M.M. Iqbal M. Pyrrole: An insight into recent pharmacological advances with structure activity relationship. Eur. J. Med. Chem. 2018 157 527 561 10.1016/j.ejmech.2018.08.002 30119011
    [Google Scholar]
  79. Ivan B.C. Barbuceanu S.F. Hotnog C.M. Anghel A.I. Ancuceanu R.V. Mihaila M.A. Brasoveanu L.I. Shova S. Draghici C. Olaru O.T. Nitulescu G.M. Dinu M. Dumitrascu F. New pyrrole derivatives as promising biological agents: Design, synthesis, characterization, in silico, and Cytotoxicity Evaluation. Int. J. Mol. Sci. 2022 23 16 8854 10.3390/ijms23168854 36012121
    [Google Scholar]
  80. Shi T. Yin G. Wang X. Xiong Y. Peng Y. Li S. Zeng Y. Wang Z. Recent advances in the syntheses of pyrroles. Green Synth. Catal. 2023 4 1 20 34 10.1016/j.gresc.2022.06.004
    [Google Scholar]
  81. Mateev E. Irfan A. Mateeva A.D. Georgieva M. Zlatkov A. Microwave-assisted organic synthesis of pyrroles. Pharmacia 2024 71 1 10 10.3897/pharmacia.71.e138859
    [Google Scholar]
  82. Yadav R. Sanduja M. Kumar V. Sharma K. Khan S. Kumar K. Microwave‐Assisted Synthetic Pathways of Pyrrole: A Comprehensive Review. Asian J. Org. Chem. 2024 13 12 e202400401 10.1002/ajoc.202400401
    [Google Scholar]
  83. Manta S. Gkaragkouni D.N. Kaffesaki E. Gkizis P. Hadjipavlou-Litina D. Pontiki E. Balzarini J. Dehaen W. Komiotis D. A novel and easy two-step, microwave-assisted method for the synthesis of halophenyl pyrrolo[2,3-b]quinoxalines via their pyrrolo precursors. Evaluation of their bioactivity. Tetrahedron Lett. 2014 55 11 1873 1876 10.1016/j.tetlet.2014.01.106
    [Google Scholar]
  84. Kamel M.S. Belal A. Aboelez M.O. Shokr E.K. Abdel-Ghany H. Mansour H.S. Shawky A.M. El-Remaily M.A.E.A.A.A. Microwave-Assisted Synthesis, Biological Activity Evaluation, Molecular Docking, and ADMET Studies of Some Novel Pyrrolo [2,3-b] Pyrrole Derivatives. Molecules 2022 27 7 2061 10.3390/molecules27072061 35408463
    [Google Scholar]
  85. Kumar S. Kumar A. Kumar N. Roy P. Sondhi S.M. Grinding and Microwave‐assisted Synthesis of Heterocyclic Molecules in High Yields and Their Biological Evaluation. J. Heterocycl. Chem. 2016 53 6 1761 1770 10.1002/jhet.2481
    [Google Scholar]
  86. Quiroga D. Torres-Cortés S. Coy-Barrera E. Microwave-Assisted Synthesis of 1-(5-Substituted-4-hydroxy-2-methyl-1H-pyrrol-3-yl)ethan-1-ones from 2-Amino Acid-Derived Enamine-Type Schiff Bases. Molbank 2025 2025 1 M1975 10.3390/M1975
    [Google Scholar]
  87. Raimondi M.V. Listro R. Cusimano M.G. La Franca M. Faddetta T. Gallo G. Schillaci D. Collina S. Leonchiks A. Barone G. Pyrrolomycins as antimicrobial agents. Microwave-assisted organic synthesis and insights into their antimicrobial mechanism of action. Bioorg. Med. Chem. 2019 27 5 721 728 10.1016/j.bmc.2019.01.010 30711310
    [Google Scholar]
  88. Raimondi M.V. Cascioferro S. Schillaci D. Petruso S. Synthesis and antimicrobial activity of new bromine-rich pyrrole derivatives related to monodeoxypyoluteorin. Eur. J. Med. Chem. 2006 41 12 1439 1445 10.1016/j.ejmech.2006.07.009 17000033
    [Google Scholar]
  89. Raimondi M.V. Schillaci D. Petruso S. Synthesis and anti‐staphylococcal activity of new halogenated pyrroles related to Pyrrolomycins F. J. Heterocycl. Chem. 2007 44 6 1407 1411 10.1002/jhet.5570440626
    [Google Scholar]
  90. Baral N. Mishra D.R. Mishra N.P. Mohapatra S. Raiguru B.P. Panda P. Nayak S. Nayak M. Kumar P.S. Microwave‐assisted rapid and efficient synthesis of chromene‐fused pyrrole derivatives through multicomponent reaction and evaluation of antibacterial activity with molecular docking investigation. J. Heterocycl. Chem. 2020 57 2 575 589 10.1002/jhet.3773
    [Google Scholar]
  91. Giguere R.J. Bray T.L. Duncan S.M. Majetich G. Application of commercial microwave ovens to organic synthesis. Tetrahedron Lett. 1986 27 41 4945 4948 10.1016/S0040‑4039(00)85103‑5
    [Google Scholar]
  92. Priecel P. Lopez-Sanchez J.A. Advantages and Limitations of Microwave Reactors: From Chemical Synthesis to the Catalytic Valorization of Biobased Chemicals. ACS Sustain. Chem.& Eng. 2019 7 1 3 21 10.1021/acssuschemeng.8b03286
    [Google Scholar]
  93. Dąbrowska S. Chudoba T. Wojnarowicz J. Łojkowski W. Current Trends in the Development of Microwave Reactors for the Synthesis of Nanomaterials in Laboratories and Industries: A Review. Crystals (Basel) 2018 8 10 379 10.3390/cryst8100379
    [Google Scholar]
  94. Kremsner J.M. Stadler A. Kappe C.O. The Scale-Up of Microwave-Assisted Organic Synthesis. Microwave Methods in Organic Synthesis. Larhed M. Olofssonq K. Berlin, Heidelberg Springer 2006 233 278 10.1007/128_048
    [Google Scholar]
  95. Henary M. Kananda C. Rotolo L. Savino B. Owens E.A. Cravotto G. Benefits and applications of microwave-assisted synthesis of nitrogen containing heterocycles in medicinal chemistry. RSC Advances 2020 10 24 14170 14197 10.1039/D0RA01378A 35498463
    [Google Scholar]
  96. Shaikh A. Application of Microwaves in Sustainable Organic Synthesis. Green Chemistry. Török B. Dransfield T. Elsevier 2018 647 671 10.1016/B978‑0‑12‑809270‑5.00023‑6
    [Google Scholar]
  97. Negi A. Alex J.M. Amrutkar S.M. Baviskar A.T. Joshi G. Singh S. Banerjee U.C. Kumar R. Imine/amide–imidazole conjugates derived from 5-amino-4-cyano-N1-substituted benzyl imidazole: Microwave-assisted synthesis and anticancer activity via selective topoisomerase-II-α inhibition. Bioorg. Med. Chem. 2015 23 17 5654 5661 10.1016/j.bmc.2015.07.020 26216018
    [Google Scholar]
  98. Sultana S. P P. Gupta J.K. B R. Barmavatu P. Mohanty D. Hybrids of imidazole with indoline derivatives: Microwave assisted synthesis, molecular docking studies, possible biological activities. J. Indian Chem. Soc. 2024 101 4 101143 10.1016/j.jics.2024.101143
    [Google Scholar]
  99. Satyanarayana V.S.V. Rakshit M. Sivakumar A. Microwave-assisted synthesis of 2,4,5-triphenyl-1h-imidazole containing schiff base derivatives with potential antioxidant and anticancer activities. Asian J. Chem. 2011 23 3 1212 1218
    [Google Scholar]
  100. Perozo-Rondón E. Costarrosa L. Martín-Aranda R.M. Rojas-Cervantes M.L. Vicente-Rodríguez M.A. Microwave enhanced synthesis of N-propargyl derivatives of imidazole. Appl. Surf. Sci. 2006 252 17 6067 6070 10.1016/j.apsusc.2005.11.005
    [Google Scholar]
  101. Banoon Z.R. Mahmood R.S. Hamad A.R. Hussein Z.A. Design, microwave synthesis, characterization and antimicrobial activity of imidazolone derivatives. J. Mol. Struct. 2025 1322 140701 10.1016/j.molstruc.2024.140701
    [Google Scholar]
  102. Chawla A. Vk K. Microwave assisted one pot synthesis and antimicrobial activity of 2-(3′-Acetyl-2′-Methyl-5′-Phenyl)-Pyrrol-1-Yl-1,4,5-Triphenyl-1h-Imidazole derivatives. Pharma Chem. 2018 10 2 27 31
    [Google Scholar]
  103. Engberg O. Saha Roy D. Krupa P. Banerjee S. Chaudhary A. Smith A.A. Li M.S. Maiti S. Huster D. Molecules in the Serotonin-Melatonin Synthesis Pathway Have Distinct Interactions with Lipid Membranes. J. Phys. Chem. B 2025 129 10 2687 2700 10.1021/acs.jpcb.4c08750 40017165
    [Google Scholar]
  104. Mohammadi Ziarani G. Moradi R. Ahmadi T. Lashgari N. Recent advances in the application of indoles in multicomponent reactions. RSC Advances 2018 8 22 12069 12103 10.1039/C7RA13321A 35539427
    [Google Scholar]
  105. Baruah B. Naidu P.S. Borah P. Bhuyan P.J. Synthesis of 5-alkylated barbituric acids and 3-alkylated indoles via microwave-assisted three-component reactions in solvent-free conditions using Hantzsch 1,4-dihydropyridines as reducing agents. Mol. Divers. 2012 16 2 291 298 10.1007/s11030‑012‑9359‑0 22297663
    [Google Scholar]
  106. Ashok D. Thara G. Kumar B.K. Srinivas G. Ravinder D. Vishnu T. Sarasija M. Sushmitha B. Microwave-assisted synthesis, molecular docking studies of 1,2,3-triazole-based carbazole derivatives as antimicrobial, antioxidant and anticancer agents. RSC Advances 2022 13 1 25 40 10.1039/D2RA05960F 36545291
    [Google Scholar]
  107. Gupta R. Jain A. Madan Y. Menghani E. A “One Pot,” Environmentally Friendly, Multicomponent Synthesis of 2‐Amino‐5‐cyano‐4‐[(2‐aryl)‐1 H ‐indol‐3‐yl]‐6‐hydroxypyrimidines and Their Antimicrobial Activity. J. Heterocycl. Chem. 2014 51 5 1395 1403 10.1002/jhet.1796
    [Google Scholar]
  108. Wen Z. Xu J. Wang Z. Qi H. Xu Q. Bai Z. Zhang Q. Bao K. Wu Y. Zhang W. 3-(3,4,5-Trimethoxyphenylselenyl)-1H-indoles and their selenoxides as combretastatin A-4 analogs: Microwave-assisted synthesis and biological evaluation. Eur. J. Med. Chem. 2015 90 184 194 10.1016/j.ejmech.2014.11.024 25461319
    [Google Scholar]
  109. Müller T. Panther J. Three- and four-component syntheses of 3-arylmethylindoles by microwave-assisted one-pot heck isomerization–fischer indolization (Alkylation) (HIFI and HIFIA) Sequences. Synthesis 2016 48 7 974 986 10.1055/s‑0035‑1561349
    [Google Scholar]
  110. Mali P.R. Chandrasekhara Rao L. Bangade V.M. Shirsat P.K. George S.A. Jagadeesh babu N. Meshram H.M. A convenient and rapid microwave-assisted synthesis of spirooxindoles in aqueous medium and their antimicrobial activities. New J. Chem. 2016 40 3 2225 2232 10.1039/C5NJ02126J
    [Google Scholar]
  111. Biradar J.S. Sasidhar B.S. Solvent-free, microwave assisted Knoevenagel condensation of novel 2,5-disubstituted indole analogues and their biological evaluation. Eur. J. Med. Chem. 2011 46 12 6112 6118 10.1016/j.ejmech.2011.10.004 22014995
    [Google Scholar]
  112. Brishty S.R. Hossain M.J. Khandaker M.U. Faruque M.R.I. Osman H. Rahman S.M.A. A Comprehensive Account on Recent Progress in Pharmacological Activities of Benzimidazole Derivatives. Front. Pharmacol. 2021 12 762807 10.3389/fphar.2021.762807 34803707
    [Google Scholar]
  113. Weber J. Antonietti M. Thomas A. Mesoporous Poly(benzimidazole) Networks via Solvent Mediated Templating of Hard Spheres. Macromolecules 2007 40 4 1299 1304 10.1021/ma062598m
    [Google Scholar]
  114. Dhiman N. Kaur K. Jaitak V. Tetrazoles as anticancer agents: A review on synthetic strategies, mechanism of action and SAR studies. Bioorg. Med. Chem. 2020 28 15 115599 10.1016/j.bmc.2020.115599 32631569
    [Google Scholar]
  115. El-Hameed R.H.A. Fatahala S.S. Sayed A.I. Synthesis of some novel benzimidazole derivatives as anticancer agent and evaluation for CDK2 inhibition activity. Med. Chemistr 2022 18 2 10.2174/1573406417666210304100830
    [Google Scholar]
  116. Shibuya M. Vascular Endothelial Growth Factor (VEGF) and Its Receptor (VEGFR) Signaling in Angiogenesis: A Crucial Target for Anti- and Pro-Angiogenic Therapies. Genes Cancer 2011 2 12 1097 1105 10.1177/1947601911423031 22866201
    [Google Scholar]
  117. Wu Y. Sun J. Lin Q. Wang D. Hai J. Sustained release of vascular endothelial growth factor A and basic fibroblast growth factor from nanofiber membranes reduces oxygen/glucose deprivation-induced injury to neurovascular units. Neural Regen. Res. 2024 19 4 887 894 10.4103/1673‑5374.382252 37843225
    [Google Scholar]
  118. Çevik U.A. Celik I. Görgülü Ş. Şahin İnan Z.D. Bostancı H.E. Karayel A. Özkay Y. Kaplancıklı Z.A. Novel benzimidazole–oxadiazole derivatives as anticancer agents with VEGFR2 Inhibitory activity: Design, synthesis, in vitro anticancer evaluation, and in silico studies. ACS Omega 2025 10 7 6801 6813 10.1021/acsomega.4c08885 40028103
    [Google Scholar]
  119. Regiec A. Machoń Z. Miedzybrodzki R. Szymaniec S. New isothiazole derivatives: synthesis, reactivity, physicochemical properties and pharmacological activity. Arch. Pharm. (Weinheim) 2006 339 7 401 413 10.1002/ardp.200500040 16838283
    [Google Scholar]
  120. de la Hoz A. Díaz-Ortiz Á. Moreno A. Microwaves in organic synthesis. Thermal and non-thermal microwave effects. Chem. Soc. Rev. 2005 34 2 164 178 10.1039/B411438H 15672180
    [Google Scholar]
  121. Kappe C.O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 2004 43 46 6250 6284 10.1002/anie.200400655 15558676
    [Google Scholar]
  122. Perreux L. Loupy A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 2001 57 45 9199 9223 10.1016/S0040‑4020(01)00905‑X
    [Google Scholar]
  123. Alamgir M. Black D.St.C. Kumar N. Synthesis, reactivity and biological activity of benzimidazoles. Bioactive Heterocycles III. Khan M.T.H. Berlin, Heidelberg Springer 2007 87 118 10.1007/7081_2007_088
    [Google Scholar]
  124. Navarrete-Vázquez G. Moreno-Diaz H. Aguirre-Crespo F. León-Rivera I. Villalobos-Molina R. Muñoz-Muñiz O. Estrada-Soto S. Design, microwave-assisted synthesis, and spasmolytic activity of 2-(alkyloxyaryl)-1H-benzimidazole derivatives as constrained stilbene bioisosteres. Bioorg. Med. Chem. Lett. 2006 16 16 4169 4173 10.1016/j.bmcl.2006.05.082 16784847
    [Google Scholar]
  125. Yan L. Fu J. Li S. Zhang J. Wang S. Gu Q. Zhang Y. Lin F. Microwave-assisted catalyzed synthesis and in vitro bioactivity evaluation of benzimidazoles bearing phenolic hydroxyl. Chem. Res. Chin. Univ. 2021 37 3 639 646 10.1007/s40242‑020‑0274‑0
    [Google Scholar]
  126. Lin S.Y. Isome Y. Stewart E. Liu J.F. Yohannes D. Yu L. Microwave-assisted one step high-throughput synthesis of benzimidazoles. Tetrahedron Lett. 2006 47 17 2883 2886 10.1016/j.tetlet.2006.02.127
    [Google Scholar]
  127. Naeimi H. Babaei Z. Microwave-assisted practical and simple method for heterocyclization of o -phenylenediamine and aldehydes using DDQ as oxidant agent. Green Chem. Lett. Rev. 2017 10 3 129 133 10.1080/17518253.2017.1314555
    [Google Scholar]
  128. Borowski P. Deinert J. Schalinski S. Bretner M. Ginalski K. Kulikowski T. Shugar D. Halogenated benzimidazoles and benzotriazoles as inhibitors of the NTPase/helicase activities of hepatitis C and related viruses. Eur. J. Biochem. 2003 270 8 1645 1653 10.1046/j.1432‑1033.2003.03540.x 12694177
    [Google Scholar]
  129. Jamkhandi D. C. M.; Disouza, J. Benzotriazole Derivatives as Antimicrobial Agents. Asian Journal of Biochemical and Pharmaceutical Research 2012 3 123 130
    [Google Scholar]
  130. He F. Liu X. Wang B. Li Z.M. Synthesis and biological activity of new 1-[4-(substituted)-piperazin-1-ylmethyl]-1H-benzotriazole. J. Chem. Res. 2006 2006 12 809 811 10.3184/030823406780199703
    [Google Scholar]
  131. Borude V.A. Moon M.S.A. Review On A Synthesis of Benzotriazole. International Journal of Advance Research and Innovative Ideas in Education 2024 10 2 4822 4837
    [Google Scholar]
  132. Nanjunda Swamy S. Basappa Sarala G. Priya B.S. Gaonkar S.L. Shashidhara Prasad J. Rangappa K.S. Microwave-assisted synthesis of N-alkylated benzotriazole derivatives: Antimicrobial studies. Bioorg. Med. Chem. Lett. 2006 16 4 999 1004 10.1016/j.bmcl.2005.10.084 16298529
    [Google Scholar]
  133. Mohanan K. Kumari B.S. Rijulal G. Microwave assisted synthesis, spectroscopic, thermal, and antifungal studies of some lanthanide(III) complexes with a heterocyclic bishydrazone. J. Rare Earths 2008 26 1 16 21 10.1016/S1002‑0721(08)60028‑9
    [Google Scholar]
  134. Mahajan K. Fahmi N. Vir Singh R. Synthesis, Characterization and Antimicrobial Studies of Sb(III) Complexes of Substituted Thioimines. Indian J. Chem. 2007 46 1221 1225
    [Google Scholar]
  135. Katritzky A.R. Singh S.K. Microwave-assisted heterocyclic synthesis. ARKIVOC 2003 2003 13 68 86 10.3998/ark.5550190.0004.d09
    [Google Scholar]
  136. Shah J.J. Mohanraj K. Comparison of conventional and microwave-assisted synthesis of benzotriazole derivatives. Indian J. Pharm. Sci. 2014 76 1 46 53 24799738
    [Google Scholar]
  137. Banik B.K. Becker F.F. Banik I. Synthesis of anticancer β-lactams: mechanism of action. Bioorg. Med. Chem. 2004 12 10 2523 2528 10.1016/j.bmc.2004.03.033 15110834
    [Google Scholar]
  138. Chavan A.A. Pai N.R. Synthesis and biological activity of N-substituted-3-chloro-2-azetidinones. Molecules 2007 12 11 2467 2477 10.3390/12112467 18065951
    [Google Scholar]
  139. Dubey A. Srivastava S.K. Srivastava S.D. Conventional and microwave assisted synthesis of 2-oxo-4-substituted aryl-azetidine derivatives of benzotriazole: A new class of biological compounds. Bioorg. Med. Chem. Lett. 2011 21 1 569 573 10.1016/j.bmcl.2010.10.057 21130647
    [Google Scholar]
  140. Suma B. V. Natesh N. N. Madhavan V. Benzotriazole in medicinal chemistry: An overview. J. Chem. Pharm. Res. 2011
    [Google Scholar]
  141. Kirti R. Characjit K. Pardeep Kumar S. Rajesh K. Gurvinder S. Microwave assisted synthesis of N-substituted benzylidene-2-(1H-benzotriazol-1-yl) acetohydrazide derivatives as antibacterial agents. Res. J. Phar. Technol. 2021 14 2 823 827 10.5958/0974‑360X.2021.00145.1
    [Google Scholar]
  142. Alraqa S.Y. Alharbi K. Aljuhani A. Rezki N. Aouad M.R. Ali I. Design, click conventional and microwave syntheses, DNA binding, docking and anticancer studies of benzotriazole-1,2,3-triazole molecular hybrids with different pharmacophores. J. Mol. Struct. 2021 1225 129192 10.1016/j.molstruc.2020.129192
    [Google Scholar]
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