Studies on Heterocyclic Compounds. XXVIII. Synthesis of 5-(3-Pyridyl)-and 5-(3-Quinolyl)furfural Derivatives

Abstract

5-(3-Pyridyl)furfural (I) and 5-(3-quinolyl)furfural (II) were condensed with ο-aminophenol, ο-aminothiophenol, or ο-phenylenediamine, followed by oxidative cyclization with lead tetraacetate to the corresponding benzoazole derivatives. I and II gave 5-(3-pyridyl)- and 5-(3-quinolyl)-2-furylvinylene derivatives, respectively, by the Wittig reaction, and I reacted with 4-nitrobenzyltriphenylphosphonium bromide to give two geometric isomers.