A novel synthesis of 3-nitroindoles via electrocyclization of 2,3-(dialk-1-enyl)4-nitropyrroles

被引：26

作者：

ten Have, R ^{[1
]}

van Leusen, AM ^{[1
]}

机构：

[1] Univ Groningen, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

TETRAHEDRON | 1998年 / 54卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(97)10405-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Nitroindoles (10) are prepared in good yields via a thermal 6 pi-electrocyclization of 2,3-(dialkenyl)-4-nitropyrroles (4) in nitrobenzene, a solvent which causes in situ aromatization of the initially formed dihydroindoles (8). The corresponding reaction of 2-alkenyl-3-alkadienyl-4-nitropyrroles (5) also leads to 3-nitroindoles (11), however, now together with 3-nitrotetrahydroindole derivatives (12). The latter compounds are formed by a tandem 6 pi-electrocyclization - intramolecular Diels-Alder reaction, and are the predominant (or only) products when nitrobenzene is replaced by triglyme. (C) 1997, Elsevier Science Ltd. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1913 / 1920

页数：8

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