Ultrasound-assisted Synthesis of β-(N-arylamino)acrylates Derivatives, Key Intermediates of Biopotent Compounds

Gabriel de Oliveira Costa; Victor Facchinetti; Gabriel Oliveira Guimarães Fernandes; Alexandra Mitidieri Bastos Mol Pimentel; Claudia Regina Brandão Gomes; James Lewis Wardell; Solange Maria Silva Veloso Wardell; Marcus Vinícius Nora de Souza

doi:10.2174/0115701786305078240521085708

ISSN: 1570-1786
E-ISSN: 1875-6255

Ultrasound-assisted Synthesis of β-(N-arylamino)acrylates Derivatives, Key Intermediates of Biopotent Compounds
Authors: Gabriel de Oliveira Costa¹, Victor Facchinetti¹, Gabriel Oliveira Guimarães Fernandes¹, Alexandra Mitidieri Bastos Mol Pimentel¹, Claudia Regina Brandão Gomes¹, James Lewis Wardell¹, Solange Maria Silva Veloso Wardell¹ and Marcus Vinícius Nora de Souza¹
View Affiliations Hide Affiliations

¹ Departamento de Síntese de Fármacos e Bioativos, Farmanguinhos/Fiocruz, R. Sizenando Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil
Source: Letters in Organic Chemistry, Volume 22, Issue 1, Jan 2025, p. 61 - 69
DOI: https://doi.org/10.2174/0115701786305078240521085708
- Received: 19 Feb 2024
- Accepted: 29 Apr 2024
- Available online: 28 May 2024

Abstract

β-(N-arylamino)acrylates are building blocks of great industrial interest as they allow the obtention of a variety of heterocyclic substances, such as quinoline and pyridone derivatives. Therefore, the development of new methodologies for the synthesis of these substances is still of interest. In this work, fourteen β-(N-arylamino)acrylates were synthesized in a multigram scale from the reaction of mono- and di-substituted anilines with diethyl ethoxymethylenemalonate by sonochemistry (US) and the results compared to those obtained by conventional heating. The use of the US brought many benefits to these syntheses, including faster reactions and increased yields. The crystal structure of diethyl 2-(((2-chloro-5-nitrophenyl)amino)methylene)malonate is also reported.

Article metrics loading...

/content/journals/loc/10.2174/0115701786305078240521085708

2024-05-28

2025-10-02

From This Site

/content/journals/loc/10.2174/0115701786305078240521085708

dcterms_title,dcterms_subject,pub_keyword

-contentType:Contributor -contentType:Concept -contentType:Institution

10

5

Full text loading...

References

Serrano-Aroca, Á.; Deb, S., Eds.; Acrylate Polymers for Advanced Applications.LondonIntechOpen202010.5772/intechopen.77563
[Google Scholar]
PenzelE. BallardN. AsuaJ.M. Polyacrylates.Hoboken, New JerseyWiley202310.1002/14356007.a21_157
[Google Scholar]
LochheadR.Y. Cosmetic Nanotechnology.Washington, D.CACS Publications200710.1021/bk‑2007‑0961.ch001
[Google Scholar]
LakshmideviA. NaiduB Sustainable Chem. Pharm.20222510061010.1016/j.scp.2022.100610
[Google Scholar]
LiuS. LiJ. LinJ. LiuF. LiuT. HuangC. Org. Biomol. Chem.20201861130113410.1039/C9OB02456E31956881
[Google Scholar]
GoleaL. ChebakiR. LaabassiM. MossetP. Chem. Data Collect.20234310097710.1016/j.cdc.2022.100977
[Google Scholar]
ChangC.C. ChangY.C. LuW.Y. LaiY.C. WuK.H. LinY.F. ChenH.Y. Eur. Polym. J.201911539940810.1016/j.eurpolymj.2019.03.055
[Google Scholar]
WangZ. VinceR. Bioorg. Med. Chem. Lett.20081841293129610.1016/j.bmcl.2008.01.02518226894
[Google Scholar]
KumarJ. MeenaP. SinghA. JameelE. MaqboolM. MobashirM. ShandilyaA. TiwariM. HodaN. JayaramB. Eur. J. Med. Chem.201611926027710.1016/j.ejmech.2016.04.05327227482
[Google Scholar]
MaignanJ.R. LichorowicC.L. GiarrussoJ. BlakeL.D. CasandraD. MutkaT.S. LaCrueA.N. BurrowsJ.N. WillisP.A. KyleD.E. ManetschR. J. Med. Chem.201659146943696010.1021/acs.jmedchem.6b0075927291102
[Google Scholar]
DrayeM. ChatelG. DuwaldR. Pharmaceuticals (Basel)20201322310.3390/ph1302002332024033
[Google Scholar]
MalvacioI. MarianoA.V.D. MoyanoE. Curr. Microw. Chem.201411525810.2174/2213335601666140402002204
[Google Scholar]
MajhiS. Ultrason. Sonochem.20217710566510.1016/j.ultsonch.2021.10566534298310
[Google Scholar]
da SilvaE.T. da Silva AraújoA. MoraesA.M. de SouzaM.V.N. Lett. Org. Chem.202017316516910.2174/1570178616666190123114922
[Google Scholar]
TrivediH.D. JoshiV.B. PatelB.Y. Synth. Commun.2023531182383410.1080/00397911.2023.2199358
[Google Scholar]
AppaR.M. LakshmideviJ. Siva PrasadS. MuralidharB. Ramesh NaiduB. NarasimhuluM. VenkateswarluK. Synth. Commun.2019491566410.1080/00397911.2018.1540047
[Google Scholar]
VenkateswarluK. Environ. Chem. Lett.20211953887395010.1007/s10311‑021‑01253‑4
[Google Scholar]
Barbosa-LimaG. da Silveira PintoL.S. KaiserC.R. WardellJ.L. De FreitasC.S. VieiraY.R. MarttorelliA. Cerbino NetoJ. BozzaP.T. WardellS.M.S.V. de SouzaM.V.N. SouzaT.M.L. Eur. J. Med. Chem.201712743444110.1016/j.ejmech.2017.01.00728092859
[Google Scholar]
BerningerM. ErkC. FußA. SkafJ. Al-MomaniE. IsraelI. RaschigM. GüntzelP. SamnickS. HolzgrabeU. Eur. J. Med. Chem.201815237739110.1016/j.ejmech.2018.04.05529742443
[Google Scholar]
Al-shaarA.H. Available From: https://patentimages.storage. googleapis.com/78/fb/d0/16c523e625b1de/EP0174832A 2.pdf 1984
TizD.B. SkokŽ. DurcikM. TomašičT. MašičL.P. IlašJ. ZegaA. DraskovitsG. RévészT. NyergesÁ. PálC. CruzC.D. TammelaP. ŽigonD. KikeljD. ZidarN. Eur. J. Med. Chem.201916716726929010.1016/j.ejmech.2019.02.00430776691
[Google Scholar]
AyyangarN.R. LahotiR.J. DanielT. Org. Prep. Proced. Int.198214532733110.1080/00304948209354924
[Google Scholar]
Al-ShaarA.H. BroughtonB.J. ChambersR.K. GilmourD.W. KelseyD.M. LowdenP. LuntE. LythgoeD.J. McClenaghanI. EP Patent 174832A21986
[Google Scholar]
HajimahdiZ. ZabihollahiR. AghasadeghiM.R. AshtianiS.H. ZarghiA. Med. Chem. Res.20162591861187610.1007/s00044‑016‑1631‑x
[Google Scholar]
Rigaku. Available From: https://rigaku.com/products/crystallography/x-ray-diffraction/crysalispro 2019
FarrugiaL.J. J. Appl. Cryst.199730556510.1107/S0021889897003117
[Google Scholar]
MacraeC.F. SovagoI. CottrellS.J. GalekP.T.A. McCabeP. PidcockE. PlatingsM. ShieldsG.P. StevensJ.S. TowlerM. WoodP.A. J. Appl. Cryst.202053122623510.1107/S160057671901409232047413
[Google Scholar]
SheldrickG.M. Acta Crystallogr. C Struct. Chem.20157113810.1107/S205322961402421825567568
[Google Scholar]
SpekA.L. Acta Crystallogr. D Biol. Crystallogr.200965214815510.1107/S090744490804362X19171970
[Google Scholar]
SheldrickG.M. SHELXS-97 and SHELXL-97, Program for Crystal Structure Solution and Refinement.GottingenUniversity of Gottingen1997
[Google Scholar]

/content/journals/loc/10.2174/0115701786305078240521085708

Ultrasound-assisted Synthesis of β-(N-arylamino)acrylates Derivatives, Key Intermediates of Biopotent Compounds

Lett. Org. Chem. 22, 61 (2025); https://doi.org/10.2174/0115701786305078240521085708

/content/journals/loc/10.2174/0115701786305078240521085708

Data & Media loading...

Supplements

Full experimental detail, IR, 1H NMR and ¹³C NMR spectra, HRMS-TOF, geometric parameters, crystal data, and structure refinement details. This material is provided in the “Supplementary Content” section of this article's webpage.

Article Type: Research Article

Keyword(s): building-blocks; gould-jacobs reaction; multigram; sonochemistry; synthesis; β-anilineacrylates

Ultrasound-assisted Synthesis of β-(N-arylamino)acrylates Derivatives, Key Intermediates of Biopotent Compounds

Abstract

From This Site

Full experimental detail, IR, 1H NMR and ¹³C NMR spectra, HRMS-TOF, geometric parameters, crystal data, and structure refinement details. This material is provided in the “Supplementary Content” section of this article's webpage.

Most Read This Month

Most Cited Most Cited RSS feed

Vilsmeier-Haack Cyclisation as a Facile Synthetic Route to Thieno [2,3- b] Quinolines (Part I)

Efficient Synthesis of 4-Arylmethylene-3-methylisoxazol-5(4H)-one Derivatives Catalyzed by Malic Acid

Wonderful Natural Drugs with Surprising Nutritional Values, Rheum Species, Gifts of the Nature

Novel Derivatives Based on Zerumbone Scaffold as Potential Anticancer Inhibitors

A Review on the Syntheses and Applications of the 5H-chromeno[2,3- b]pyridines

Fe Doped Ga2O3 Nanomaterial Catalysed Green and Efficient One Pot Three Component Synthesis of Tetrahydrobenzo[b]pyran

Sulfonated Ethylenediamine Functionalized Magnetic Nanoparticles as a Highly Efficient Heterogeneous Nanocatalyst for the Green Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

K2CO3/TBAB, a Composite of Inorganic and Organic Salts, a Novel and Powerful Media for Regioselective Michael Addition of Dihydropyrimidinones to Acrylic Esters Under and Without Solvent Conditions

Decomposition Kinetics of 1,1-Dihydroperoxycyclohexane in Some Organic Solvents

In Silico Screening of Some Anti-Cancer Drugs Against the Main Protease of COVID-19 Using Molecular Docking

Ultrasound-assisted Synthesis of β-(N-arylamino)acrylates Derivatives, Key Intermediates of Biopotent Compounds

Abstract

Full experimental detail, IR, 1H NMR and 13C NMR spectra, HRMS-TOF, geometric parameters, crystal data, and structure refinement details. This material is provided in the “Supplementary Content” section of this article's webpage.

Most Read This Month

Most Cited Most Cited RSS feed

Full experimental detail, IR, 1H NMR and ¹³C NMR spectra, HRMS-TOF, geometric parameters, crystal data, and structure refinement details. This material is provided in the “Supplementary Content” section of this article's webpage.