Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

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

Author(s): 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 and Marcus Vinicius Nora De Souza*

Volume 22, Issue 1, 2025

Published on: 28 May, 2024

Page: [61 - 69] Pages: 9

DOI: 10.2174/0115701786305078240521085708

open access plus

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.

« Previous Next »
[1]
Serrano-Aroca, Á.; Deb, S., Eds.; Acrylate Polymers for Advanced Applications; IntechOpen: London, 2020.
[http://dx.doi.org/10.5772/intechopen.77563]
[2]
Penzel, E.; Ballard, N.; Asua, J.M. Polyacrylates; Wiley: Hoboken, New Jersey, 2023.
[http://dx.doi.org/10.1002/14356007.a21_157]
[3]
Lochhead, R.Y. Cosmetic Nanotechnology; ACS Publications: Washington, D.C, 2007.
[http://dx.doi.org/10.1021/bk-2007-0961.ch001]
[4]
Lakshmidevi, A.; Naidu, B Sustainable Chem. Pharm., 2022, 25, 100610.
[http://dx.doi.org/10.1016/j.scp.2022.100610]
[5]
Liu, S.; Li, J.; Lin, J.; Liu, F.; Liu, T.; Huang, C. Org. Biomol. Chem., 2020, 18(6), 1130-1134.
[http://dx.doi.org/10.1039/C9OB02456E] [PMID: 31956881]
[6]
Golea, L.; Chebaki, R.; Laabassi, M.; Mosset, P. Chem. Data Collect., 2023, 43, 100977.
[http://dx.doi.org/10.1016/j.cdc.2022.100977]
[7]
Chang, C.C.; Chang, Y.C.; Lu, W.Y.; Lai, Y.C.; Wu, K.H.; Lin, Y.F.; Chen, H.Y. Eur. Polym. J., 2019, 115, 399-408.
[http://dx.doi.org/10.1016/j.eurpolymj.2019.03.055]
[8]
Wang, Z.; Vince, R. Bioorg. Med. Chem. Lett., 2008, 18(4), 1293-1296.
[http://dx.doi.org/10.1016/j.bmcl.2008.01.025] [PMID: 18226894]
[9]
Kumar, J.; Meena, P.; Singh, A.; Jameel, E.; Maqbool, M.; Mobashir, M.; Shandilya, A.; Tiwari, M.; Hoda, N.; Jayaram, B. Eur. J. Med. Chem., 2016, 119, 260-277.
[http://dx.doi.org/10.1016/j.ejmech.2016.04.053] [PMID: 27227482]
[10]
Maignan, J.R.; Lichorowic, C.L.; Giarrusso, J.; Blake, L.D.; Casandra, D.; Mutka, T.S.; LaCrue, A.N.; Burrows, J.N.; Willis, P.A.; Kyle, D.E.; Manetsch, R. J. Med. Chem., 2016, 59(14), 6943-6960.
[http://dx.doi.org/10.1021/acs.jmedchem.6b00759] [PMID: 27291102]
[11]
Draye, M.; Chatel, G.; Duwald, R. Pharmaceuticals (Basel), 2020, 13(2), 23.
[http://dx.doi.org/10.3390/ph13020023] [PMID: 32024033]
[12]
Malvacio, I.; Mariano, A.V.D.; Moyano, E. Curr. Microw. Chem., 2014, 1(1), 52-58.
[http://dx.doi.org/10.2174/2213335601666140402002204]
[13]
Majhi, S. Ultrason. Sonochem., 2021, 77, 105665.
[http://dx.doi.org/10.1016/j.ultsonch.2021.105665] [PMID: 34298310]
[14]
da Silva, E.T.; da Silva Araújo, A.; Moraes, A.M.; de Souza, M.V.N. Lett. Org. Chem., 2020, 17(3), 165-169.
[http://dx.doi.org/10.2174/1570178616666190123114922]
[15]
Trivedi, H.D.; Joshi, V.B.; Patel, B.Y. Synth. Commun., 2023, 53(11), 823-834.
[http://dx.doi.org/10.1080/00397911.2023.2199358]
[16]
Appa, R.M.; Lakshmidevi, J.; Siva Prasad, S.; Muralidhar, B.; Ramesh Naidu, B.; Narasimhulu, M.; Venkateswarlu, K. Synth. Commun., 2019, 49(1), 56-64.
[http://dx.doi.org/10.1080/00397911.2018.1540047]
[17]
Venkateswarlu, K. Environ. Chem. Lett., 2021, 19(5), 3887-3950.
[http://dx.doi.org/10.1007/s10311-021-01253-4]
[18]
Barbosa-Lima, G.; da Silveira Pinto, L.S.; Kaiser, C.R.; Wardell, J.L.; De Freitas, C.S.; Vieira, Y.R.; Marttorelli, A.; Cerbino Neto, J.; Bozza, P.T.; Wardell, S.M.S.V.; de Souza, M.V.N.; Souza, T.M.L. Eur. J. Med. Chem., 2017, 127, 434-441.
[http://dx.doi.org/10.1016/j.ejmech.2017.01.007] [PMID: 28092859]
[19]
Berninger, M.; Erk, C.; Fuß, A.; Skaf, J.; Al-Momani, E.; Israel, I.; Raschig, M.; Güntzel, P.; Samnick, S.; Holzgrabe, U. Eur. J. Med. Chem., 2018, 152, 377-391.
[http://dx.doi.org/10.1016/j.ejmech.2018.04.055] [PMID: 29742443]
[20]
Al-shaar, A.H. 1984. Available From: https://patentimages.storage. googleapis.com/78/fb/d0/16c523e625b1de/EP0174832A 2.pdf
[21]
Tiz, D.B.; Skok, Ž.; Durcik, M.; Tomašič, T.; Mašič, L.P.; Ilaš, J.; Zega, A.; Draskovits, G.; Révész, T.; Nyerges, Á.; Pál, C.; Cruz, C.D.; Tammela, P.; Žigon, D.; Kikelj, D.; Zidar, N. Eur. J. Med. Chem., 2019, 167(167), 269-290.
[http://dx.doi.org/10.1016/j.ejmech.2019.02.004] [PMID: 30776691]
[22]
Ayyangar, N.R.; Lahoti, R.J.; Daniel, T. Org. Prep. Proced. Int., 1982, 14(5), 327-331.
[http://dx.doi.org/10.1080/00304948209354924]
[23]
Al-Shaar, A.H.; Broughton, B.J.; Chambers, R.K.; Gilmour, D.W.; Kelsey, D.M.; Lowden, P.; Lunt, E.; Lythgoe, D.J.; McClenaghan, I. EP Patent 174832A2, 1986.
[24]
Hajimahdi, Z.; Zabihollahi, R.; Aghasadeghi, M.R.; Ashtiani, S.H.; Zarghi, A. Med. Chem. Res., 2016, 25(9), 1861-1876.
[http://dx.doi.org/10.1007/s00044-016-1631-x]
[25]
Rigaku. 2019. Available From: https://rigaku.com/products/crystallography/x-ray-diffraction/crysalispro
[26]
Farrugia, L.J. J. Appl. Cryst., 1997, 30(5), 565.
[http://dx.doi.org/10.1107/S0021889897003117]
[27]
Macrae, C.F.; Sovago, I.; Cottrell, S.J.; Galek, P.T.A.; McCabe, P.; Pidcock, E.; Platings, M.; Shields, G.P.; Stevens, J.S.; Towler, M.; Wood, P.A. J. Appl. Cryst., 2020, 53(1), 226-235.
[http://dx.doi.org/10.1107/S1600576719014092] [PMID: 32047413]
[28]
Sheldrick, G.M. Acta Crystallogr. C Struct. Chem., 2015, 71(1), 3-8.
[http://dx.doi.org/10.1107/S2053229614024218] [PMID: 25567568]
[29]
Spek, A.L. Acta Crystallogr. D Biol. Crystallogr., 2009, 65(2), 148-155.
[http://dx.doi.org/10.1107/S090744490804362X] [PMID: 19171970]
[30]
Sheldrick, G.M. SHELXS-97 and SHELXL-97, Program for Crystal Structure Solution and Refinement; University of Gottingen: Gottingen, 1997.

Rights & Permissions Print Cite
© 2025 Bentham Science Publishers | Privacy Policy