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2000
Volume 22, Issue 4
  • ISSN: 1570-1786
  • E-ISSN: 1875-6255

Abstract

A rapid and direct route for the new synthesis of various quinazolines-4 (1)-ones with appropriate yields through a three-component reaction consisting of the amine-trichloroacetonitrile adduct and isatoic anhydride is a remarkable achievement in organic chemistry. The use of CuO as the catalyst in DMF under reflux conditions at 110°C for 4 hours offers reaction conditions, which are conducive to the formation of the desired products while maintaining good selectivity. The simplicity of the one-pot synthesis and using the available raw materials contribute to the ease of purification of the synthesized quinazolines-4 (1)-ones, streamlining the overall synthetic process. The synthesized product is often found in drugs and other bioactive molecules.

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References

  1. HortonD.A. BourneG.T. SmytheM.L. Chem. Rev.2003103389393010.1021/cr020033s 12630855
    [Google Scholar]
  2. MhaskeS.B. ArgadeN.P. Tetrahedron200662429787982610.1016/j.tet.2006.07.098
    [Google Scholar]
  3. KuarmB.S. ReddyY.T. MadhavJ.V. CrooksP.A. RajithaB. Bioorg. Med. Chem. Lett.201121152452710.1016/j.bmcl.2010.10.082 21134751
    [Google Scholar]
  4. CaoS.L. FengY.P. JiangY.Y. LiuS.Y. DingG.Y. LiR.T. Bioorg. Med. Chem. Lett.20051571915191710.1016/j.bmcl.2005.01.083 15780632
    [Google Scholar]
  5. LüthA. LöِweW. Eur. J. Med. Chem.20084371478148810.1016/j.ejmech.2007.09.018 17981366
    [Google Scholar]
  6. WolfeJ.F. RathmanT.L. SleeviM.C. CampbellJ.A. GreenwoodT.D. J. Med. Chem.199033116116610.1021/jm00163a027 2296016
    [Google Scholar]
  7. AlyM.M. MohamedY.A. El-BayoukiK.A.M. BasyouniW.M. AbbasS.Y. Eur. J. Med. Chem.20104583365337310.1016/j.ejmech.2010.04.020 20510483
    [Google Scholar]
  8. KenichiO. YoshihisaY. ToyonariO. ToruI. YoshioI. J. Med. Chem.19852856857610.1021/jm50001a006 3872940
    [Google Scholar]
  9. LoweJ.A.III ArcherR.L. ChapinD.S. ChengJ.B. HelwegD. JohnsonJ.L. KoeB.K. LebelL.A. MooreP.F. NielsenJ.A. RussoL.L. ShirleyJ.T. J. Med. Chem.199134262462810.1021/jm00106a024 1995886
    [Google Scholar]
  10. BediP.M.S. KumarV. MahajanM.P. Bioorg. Med. Chem. Lett.200414205211521310.1016/j.bmcl.2004.07.065 15380229
    [Google Scholar]
  11. TereshimaK. ShimamuraH. KawaseA. TanakaY. TanimuraT. KamisakiT. IshizukaY. SatoM. Chem. Pharm. Bull.1995432021202310.1248/cpb.43.2021 8575039
    [Google Scholar]
  12. LiH. HuangR. QiuD. YangZ. LiuX. MaJ. Ma.Z. Prog. Nat. Sci.19988359365
    [Google Scholar]
  13. MalamasM.S. MillenJ. J. Med. Chem.19913441492150310.1021/jm00108a038 1901912
    [Google Scholar]
  14. ChandrikaP.M. YakaiahT. NarsaiahB. SridharV. VenugopalG. RaoJ.V. KumarK.P. MurthyU.S.N. RaoA.R.R. Indian J. Chem.200948840847
    [Google Scholar]
  15. ChawlaA. BatraC. Int. Res. J. Pharm.201343495810.7897/2230‑8407.04309
    [Google Scholar]
  16. JoshiB.S. NewtonM.G. LeeD.W. BarberA.D. PelletierS.W. Tetrahedron Asymmetry199671252810.1016/0957‑4166(95)00412‑2
    [Google Scholar]
  17. ChatterjeeA. GangulyM. Phytochemistry19687230731110.1016/S0031‑9422(00)86329‑3
    [Google Scholar]
  18. GhosalS. ChauhanR.B.P.S. MehtaR. Phytochemistry197514383083210.1016/0031‑9422(75)83057‑3
    [Google Scholar]
  19. MitscherL.A. WongW.C. De MeulenereT. SulkoJ. DrakeS. Heterocycles1981151017102110.3987/S‑1981‑02‑1017
    [Google Scholar]
  20. WittA. BergmanJ. Curr. Org. Chem.20037765967710.2174/1385272033486738
    [Google Scholar]
  21. KoepfliJ.B. MeadJ.F. BrockmanJ.A.Jr J. Am. Chem. Soc.19476971837183710.1021/ja01199a513 20251439
    [Google Scholar]
  22. O’BrienN.S. GilbertJ. McCluskeyA. SakoffJ.A. RSC Med. Chem.20241551686170810.1039/D3MD00600J 38784470
    [Google Scholar]
  23. DuttaA. SarmaD. Sustain. Chem. Pharm.20212010040210.1016/j.scp.2021.100402
    [Google Scholar]
  24. HuF. CuiX. BanZ. LuG. LuoN. HuangG. Org. Biomol. Chem.20191792356236010.1039/C9OB00020H 30758386
    [Google Scholar]
  25. OzakiK. YamadaY. OineT. IshizukaT. IwasawaY. J. Med. Chem.198528556857610.1021/jm50001a006 3872940
    [Google Scholar]
  26. BonolaG. Da ReP. MagistrettiM.J. MassaraniE. J. Med. Chem.1968111136113910.1021/jm00312a007 5680025
    [Google Scholar]
  27. HourM.J. HuangL.J. KuoS.C. XiaY. BastowK. NakanishiY. HamelE. LeeK.H. J. Med. Chem.200043234479448710.1021/jm000151c 11087572
    [Google Scholar]
  28. ZhangH. LiuH. LuoX. WangY. LiuY. JinH. LiuZ. YangW. YuP. ZhangL. ZhangL. Eur. J. Med. Chem.201815223525210.1016/j.ejmech.2018.04.045 29723786
    [Google Scholar]
  29. HrastM. RožmanK. JukičM. PatinD. GobecS. SovaM. Bioorg. Med. Chem. Lett.201727153529353310.1016/j.bmcl.2017.05.064 28579123
    [Google Scholar]
  30. RomeroA.H. RodríguezN. OviedoH. Bioorg. Chem.20198314515310.1016/j.bioorg.2018.10.028 30359795
    [Google Scholar]
  31. TsengM.C. YangH.Y. ChuY.H. Org. Biomol. Chem.20108241942710.1039/B910545J 20066279
    [Google Scholar]
  32. KhanI. IbrarA. AbbasN. SaeedA. Eur. J. Med. Chem.20147619324410.1016/j.ejmech.2014.02.005 24583357
    [Google Scholar]
  33. AlagarsamyV. Raja SolomonV. DhanabalK. Bioorg. Med. Chem.200715123524110.1016/j.bmc.2006.09.065 17079148
    [Google Scholar]
  34. Ghorbani-VagheiR. ShahriariA. MaghbooliY. Mahmoudi.J. Res. Chem. Intermed.201743298399310.1007/s11164‑016‑2678‑5
    [Google Scholar]
  35. Mohammadpoor-BaltorkI. KhosropourA.R. MoghadamM. TangestaninejadS. MirkhaniV. BaghersadS. MirjafariA. C. R. Chim.2011141094495210.1016/j.crci.2011.05.003
    [Google Scholar]
  36. HutaitS. MaikhuriV.K. PandeyA.K. ShuklaP. SrivastavaS. Chem. Select20249e202304087
    [Google Scholar]
  37. HaoS. YangJ. LiuP. XuJ. YangC. LiF. Org. Lett.20212372553255810.1021/acs.orglett.1c00475 33729807
    [Google Scholar]
  38. MemarianH.R. EbrahimiS. J. Photochem. Photobiol. Chem.201327181510.1016/j.jphotochem.2013.07.008
    [Google Scholar]
  39. ZaytsevV.P. RevutskayaE.L. Kuz’menkoM.G. NovikovR.A. ZubkovF.I. SorokinaE.A. NikitinaE.V. TozeF.A.A. VarlamovA.V. Russ. Chem. Bull.20156461345135310.1007/s11172‑015‑1016‑1
    [Google Scholar]
  40. GaradD.N. VivekiA.B. MhaskeS.B. J. Org. Chem.201782126366637210.1021/acs.joc.7b00948 28523916
    [Google Scholar]
  41. LiuJ. HaoX.C. ChenY. DingS. LiuH.S. WangD. J. Chem. Res.2017411182010.3184/174751917X14815427219167
    [Google Scholar]
  42. KubicováL. ŠustrM. KráľováK. ChobotV. VytlačilováJ. JahodářL. VuorelaP. MacháčekM. KaustováJ. Molecules200381175676910.3390/81100756
    [Google Scholar]
  43. WangY. MengX. ChenG. ZhaoP. Catal. Commun.201810410611110.1016/j.catcom.2017.10.024
    [Google Scholar]
  44. WuX.F. HeL. NeumannH. BellerM. Chemistry20131938126351263810.1002/chem.201302182 24175339
    [Google Scholar]
  45. KabriY. GellisA. VanelleP. Green Chem.200911220120810.1039/B816723K
    [Google Scholar]
  46. YangX. ChengG. ShenJ. KuaiC. CuiX. Org. Chem. Front.20152436636810.1039/C4QO00260A
    [Google Scholar]
  47. MohammedS. VishwakarmaR.A. BharateS.B. J. Org. Chem.201580136915692110.1021/acs.joc.5b00989 26067767
    [Google Scholar]
  48. SharmaM. PandeyS. ChauhanK. SharmaD. KumarB. ChauhanP.M.S. J. Org. Chem.201277292993710.1021/jo2020856 22181712
    [Google Scholar]
  49. KarhaleS. SurvaseD. BhatR. UbaleP. HelaviV. Res. Chem. Intermed.20174373915392410.1007/s11164‑016‑2855‑6
    [Google Scholar]
  50. SafariJ. Gandomi-RavandiS. J. Mol. Catal. Chem.20143901610.1016/j.molcata.2014.02.013
    [Google Scholar]
  51. LathaG. DevarajanN. SureshP. Chem. Select202051004110047
    [Google Scholar]
  52. KausarN. RoyI. ChattopadhyayD. DasA.R. RSC Advances2016627223202233010.1039/C6RA00388E
    [Google Scholar]
  53. DuttaA. SarmaD. Tuberculosis202012410198610.1016/j.tube.2020.101986 32942187
    [Google Scholar]
  54. MichaelJ.P. Nat. Prod. Rep.200825116618710.1039/B612168N 18250901
    [Google Scholar]
  55. NematpourM. DastjerdiH.F. Mahboubi-RabbaniM. Lett. Org. Chem.2022191344010.2174/1570178618666210920112141
    [Google Scholar]
  56. NematpourM. DastjerdiH.F. JahaniM. TabatabaiS.A. Lett. Org. Chem.2020171183283610.2174/1570178616666190905142545
    [Google Scholar]
  57. TangL. ZhaoX. ZouG. ZhouY. YangX. Asian J. Org. Chem.20165333533910.1002/ajoc.201500512
    [Google Scholar]
  58. MekalaR. AkulaR. KamarajuR.R. BannothC.K. RegatiS. SarvaJ. Synlett201482182610.1055/s‑0033‑1340786
    [Google Scholar]
  59. ChengR. GuoT. Zhang-NegrerieD. DuY. ZhaoK. Synthesis2013452998300610.1055/s‑0033‑1338521
    [Google Scholar]
  60. WeiH. LiT. ZhouY. ZhouL. ZengQ. Synthesis2013453349335410.1055/s‑0033‑1340040
    [Google Scholar]
  61. HuB.Q. WangL.X. YangL. XiangJ.F. TangY.L. Eur. J. Org. Chem.20152015204504450910.1002/ejoc.201500473
    [Google Scholar]
  62. RomeroA.H. SalazarJ. LóَpezS.E. Synthesis.2013452043205010.1055/s‑0033‑1338854
    [Google Scholar]
  63. XuW. Org. Lett.2011131274127710.1021/ol1030266
    [Google Scholar]
  64. ZhengZ. AlperH. Org. Lett.200810582983210.1021/ol7029454 18247629
    [Google Scholar]
  65. LiuJ.F. LeeJ. DaltonA.M. BiG. YuL. BaldinoC.M. McEloryE. BrownM. Tetrahedron Lett.20054681241124410.1016/j.tetlet.2005.01.008
    [Google Scholar]
  66. NematpourM. NazariM. HosseiniO. Iran. J. Pharm. Res.20222112382612383410.5812/ijpr.123826
    [Google Scholar]
  67. YavariI. NematpourM. SodagarE. Synlett201324216116410.1055/s‑0032‑1317952
    [Google Scholar]
  68. YavariI. NematpourM. Tetrahedron Lett.201354364973497410.1016/j.tetlet.2013.07.029
    [Google Scholar]
  69. YavariI. NematpourM. Synlett201324216516810.1055/s‑0032‑1317951
    [Google Scholar]
  70. NematpourM. KohiS.R. AbediE. LotfiM. Lett. Org. Chem.20171481510.2174/1570178614666170426162522
    [Google Scholar]
  71. NematpourM. AbediE. AbediE. Lett. Org. Chem.201815867868110.2174/1570178615666171222162430
    [Google Scholar]
  72. NematpourM. AbediE. AbediE. LotfiM. Lett. Org. Chem.201815972773010.2174/1570178614666170810125505
    [Google Scholar]
  73. NematpourM. Tetrahedron202416313414510.1016/j.tet.2024.134145
    [Google Scholar]
  74. NematpourM. Chem. Select20249e20240087110.1002/slct.202400871
    [Google Scholar]
  75. YavariI. NematpourM. Synlett201324111420142210.1055/s‑0033‑1338747
    [Google Scholar]
  76. JahaniR. AbtahiS. NematpourM. Fasihi DastjerdiH. ChamanaraM. HamiZ. PaknejadB. Bioorg. Chem.202010410421210.1016/j.bioorg.2020.104212 32916390
    [Google Scholar]
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