Synthesis of some 2-phenylpyrrole derivatives

Abstract

We have made and converted some aryl cyclopropyl ketones (1) into 2-arylpyrrolidines (2) and hence to the 1-pyrrolines (3), the 3-bromo-1-pyrrolines (3d) and to the corresponding 2-arylpyrroles (4). An alternative route via the reaction of alkynes with aryloxazolones has been improved.

In particular, substituted 2-(2-methoxyphenyl)pyrroles have been made, also some chloro-analogues (5b, c) of the bromine-containing marine antibiotic, 3,4,5-tribromo-2-(3,5-dibromo-2-hydroxyphenyl)pyrrole (5d).