ChemInform Abstract: Synthesis of Highly Substituted Diphenylacetamides and Diphenylsulfonamides by the Goldberg Coupling Reaction.

Abstract

Synthesis of Highly Substituted Diphenylacetamides and Diphenylsulfonamides by the Goldberg Coupling Reaction.-Multisubstituted diphenylacetamides such as (III) and (VII) and diphenylsulfonamides like (XVI) and (XVIII), which embody 2,5-dimethyl substituents, are synthesized. The yields of coupling products are generally lower in the case of diphenylsulfonamides. Alkaline hydrolysis of the diphenylacetamides is attempted as well as the conversion of the resulting diphenylamines into the corresponding carbazoles, e.g. (IX) and (XIII). However, the yields of the desired products are very low. Thus, the general route via Goldberg coupling, hydrolysis, and cyclization by palladium acetate cannot be considered as generally useful method to synthesized new ellipticines. -(RAPOSO, M. MANUELA M.; PEREIRA, ALEXANDRA M. B.; OLIVEIRA-CAMPOS, ANA M. F.; SHAN-NON, PATRICK V. R.; J. Chem. Res., Synop. (2000) 4, 156-158; Dep. Quim., Univ. Minho, P-4700 Braga, Port.; EN)