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Paper | Regular issue | Vol 24, No. 7, 1986, pp.1943-1954
Published online, 1st January, 1970
DOI: 10.3987/R-1986-07-1943
On the Leuckart Reaction of Deoxybenzoins. Isolation and Characterization of 2,3,4,5-Tetraarypyridine Derivatives

María Jesús Villa, Ester Domínguez,* and Ester Lete

*Departamento de Física Aplicada, Facultad de Ciencias, Universidad del País Vasco, Apartado 450, 01080 Vitoria-Gasteiza, Spain

Abstract

The Leuckart reaction of deoxybenzoins has been examined. The deoxybenzoins (1b-c) possessing a phenolic substituent in the ortho position to the carbonyl group react with formamide to afford, besides the known stilbene, pyrimidine and isoflavone derivatives, 2,3,4,5-tetraarylpyridines, whose structures and formation mechanism are discussed. In contrast, the Leuckart reaction of the alkoxy substituted deoxybenzoins (1d-f) leads to the expected formamides in high yields, though always accompanied by the corresponding stilbenes and pyrimidines as by-products.