Transformations of  N -(2-acylaryl)benzamides and their analogs under the Camps cyclization conditions

S. S. Mochalov; A. N. Fedotov; E. V. Trofimova; N. S. Zefirov

doi:10.1134/S107042801607006X

Transformations of N-(2-acylaryl)benzamides and their analogs under the Camps cyclization conditions

Authors: Mochalov S.S.¹, Fedotov A.N.¹, Trofimova E.V.¹, Zefirov N.S.¹
Affiliations:
1. Faculty of Chemistry
Issue: Vol 52, No 7 (2016)
Pages: 956-969
Section: Article
URL: https://journals.rcsi.science/1070-4280/article/view/214661
DOI: https://doi.org/10.1134/S107042801607006X
ID: 214661

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Abstract

N-(2-Acylaryl)benzamides and analogous N-substituted furan-2-, thiophene-2-, and cyclopropane-carboxamides in the systems EtONa–EtOH, EtONa–THF, and t-BuOK–t-BuOH undergo Camps cyclization to 2-aryl-, 2-hetaryl-, and 2-cyclopropylquinolin-4(1H)-ones with high yields. The same substrates in the system t-BuOK (5 equiv)–THF are converted mainly to the corresponding N-(2-hydroxyaryl) amides as a result of oxidative transformation of the acyl fragment into hydroxy group.