Convergent Routes to Pyrroles Exploiting the Unusual Radical Chemistry of Xanthates – An Overview

This article is affectionately dedicated to Professor Victor Snieckus on the occasion of his 80th birthday.

Abstract

Convergent routes to a variety of pyrroles involving radical additions of xanthates are described. Emphasis is placed on reactions leading to the formation of 1,4-diketones or 1,4-ketoaldehydes or their synthetic equivalents, which can then be condensed with ammonia or primary amines in a variation of the classical Paal–Knorr synthesis of pyrroles. The modification of pyrroles by direct radical addition is also discussed.

1 Introduction

2 Earlier Routes to Pyrroles

3 The Xanthate Radical Addition–Transfer Process

4 Application to Pyrrole Synthesis

5 Further Variations

6 Direct Modification of Existing Pyrrole Rings

7 Outlook and Perspectives

Key words

pyrroles - Paal–Knorr reaction - 1,4-diketones - radical addition - xanthates

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