The Chlorination of Pyrroles. Part III

Abstract

The chlorination and subsequent demethylation of 2-(2′-methoxybenzoyl) and 2-(2′,6′-dimethoxybenzoyl)-pyrroles are described, giving deoxypyoluteorin and pyoluteorin as main products. A number of minor products of under- and overchlorination have been characterized. Alternative syntheses of some of these antibiotics are detailed. Two routes to 2,3-dichloropyrrole are given and the Friedel–Crafts reaction of this compound utilized in synthesizing deoxypyoluteorin and pyoluteorin. A number of analogs have been made and their microbiological activities compared. The monodeoxy series is generally more active.