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

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.