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Letters in Organic Chemistry

Author(s): Kalyan Maram, Kowthalam Anitha, Reddymasu Sreenivasulu and Rudraraju Ramesh Raju*

DOI: 10.2174/1570178620666221207105947

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DBU Mediated Efficient Synthesis of New N-(furan/thiophene/pyrrole-2-yl- (2-hydroxynaphthalen-1-yl)methyl)acetamides

Page: [603 - 607] Pages: 5

  • * (Excluding Mailing and Handling)

Abstract

A series of N-(furan/thiophene/pyrrole-2-yl-(2-hydroxynaphthalen-1-yl)methyl) acetamide derivatives 4 has been depicted by one-pot three-component synthesis using 2- naphthol 1 with aldehydes 2 and amides 3 in the presence of DBU as a catalyst in ethanol as solvent under reflux condition for 110-120 min. This method has the advantages of good yields, being environmentally friendly, straightforward protocol, short reaction times, and mild reaction conditions.

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[1]
Dömling, A.; Wang, W.; Wang, K. Chem. Rev., 2012, 112(6), 3083-3135.
[http://dx.doi.org/10.1021/cr100233r] [PMID: 22435608]
[2]
Levi, L.; Müller, T.J. J. Chem. Soc. Rev., 2016, 45(10), 2825-2846.
[http://dx.doi.org/10.1039/C5CS00805K]
[3]
Cioc, R.C.; Ruijter, E.; Orru, R.V.A. Green Chem., 2014, 16(6), 2958-2975.
[http://dx.doi.org/10.1039/C4GC00013G]
[4]
Chebanov, V.A.; Muravyova, E.A.; Desenko, S.M.; Musatov, V.I.; Knyazeva, I.V.; Shishkina, S.V.; Shishkin, O.V.; Kappe, C.O. J. Comb. Chem., 2006, 8(3), 427-434.
[http://dx.doi.org/10.1021/cc060021a] [PMID: 16677013]
[5]
Nilsson, B.L.; Overman, L.E. J. Org. Chem., 2006, 71(20), 7706-7714.
[http://dx.doi.org/10.1021/jo061199m] [PMID: 16995677]
[6]
Chebanov, V.A.; Saraev, V.E.; Desenko, S.M.; Chernenko, V.N.; Shishkina, S.V.; Shishkin, O.V.; Kobzar, K.M.; Kappe, C.O. Org. Lett., 2007, 9(9), 1691-1694.
[http://dx.doi.org/10.1021/ol070411l] [PMID: 17385876]
[7]
De Silva, R.A.; Santra, S.; Andreana, P.R. Org. Lett., 2008, 10(20), 4541-4544.
[http://dx.doi.org/10.1021/ol801841m] [PMID: 18811177]
[8]
Maddila, S.; Gangu, K.K.; Maddila, S.N.; Jonnalagadda, S.B. Mol. Divers., 2017, 21(1), 247-255.
[http://dx.doi.org/10.1007/s11030-016-9708-5] [PMID: 27853977]
[9]
Gangu, K.K.; Maddila, S.; Jonnalagadda, S.B. New J. Chem., 2017, 41, 6455-6463.
[http://dx.doi.org/10.1039/C7NJ00855D]
[10]
Bhaskaruni, S.; Maddila, S.; van Zyl, W.; Jonnalagadda, S. Molecules, 2018, 23(7), 1648.
[http://dx.doi.org/10.3390/molecules23071648] [PMID: 29976914]
[11]
Shabalala, S.; Maddila, S.; van Zyl, W.E.; Jonnalagadda, S.B. Catal. Commun., 2016, 79, 21-25.
[http://dx.doi.org/10.1016/j.catcom.2016.02.017]
[12]
Gangu, K.K.; Maddila, S.; Maddila, S.N.; Jonnalagadda, S.B. RSC Advances, 2017, 7(1), 423-432.
[http://dx.doi.org/10.1039/C6RA25372E]
[13]
Al´’-Assar, F.; Zelenin, K.N.; Lesiovskaya, E.E.; Bezhan, I.P.; Chakchir, B.A. Pharm. Chem. J., 2002, 36(11), 598-603.
[http://dx.doi.org/10.1023/A:1022665331722]
[14]
Rambhau, P.G. Drug Invention Today, 2013, 5, 148-152.
[http://dx.doi.org/10.1016/j.dit.2013.05.010]
[15]
Alexander, D.; Wei, W. Chem. Rev., 2012, 112, 3083-3135.
[http://dx.doi.org/10.1021/cr100233r]
[16]
Ustündağ, G.C.; Şatana, D.; Zhan, G. Enzyme inhib. Med. Chem., 2016, 31, 369-380.