Tetrahedron

Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino [6, 7-b] indoles and indoline-2-thiones

GW Rewcastle, T Janosik, J Bergman

Index: Rewcastle, Gordon W; Janosik, Tomasz; Bergman, Jan Tetrahedron, 2001 , vol. 57, # 33 p. 7185 - 7189

Full Text: HTML

Citation Number: 21

Abstract

The reactions of 2-lithiated indole and 1-methylindole with elemental sulfur have been studied, leading eg to a rational approach to pentathiepino [6, 7-b] indoles 5 and 10. Notable amounts of the previously known tetrathiocino [5, 6-b: 8, 7-b′] diindole 11 could be observed as a side reaction in the preparation of 10. Treatment of the anions of indoline-2- thiones 6 or 7 with sulfur also gave the pentathiepins 5 or 10, respectively. In addition, a ...