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

被引：22

作者：

Rewcastle, GW

Janosik, T

Bergman, J

机构：

[1] Univ Auckland, Auckland Canc Soc Res Ctr, Fac Med & Hlth Sci, Auckland 1, New Zealand

[2] Karolinska Inst, Novum, Dept Biosci, CNT,Unit Organ Chem, SE-14157 Huddinge, Sweden

[3] Sodertorn Univ Coll, SE-14104 Huddinge, Sweden

来源：

TETRAHEDRON | 2001年 / 57卷 / 33期

关键词：

lithiated indole; indole-2-thiones; pentathiepins;

D O I：

10.1016/S0040-4020(01)00660-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of 2-lithiated indole and 1-methylindole with elemental sulfur have been studied, leading e.g. 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 convenient and clean lithiation route to indoline-2-thione (6) has been developed. (C) 2001 Elsevier Science Ltd. All rights reserved.

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收藏

页码：7185 / 7189

页数：5

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