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Rearrangement of spiro[2H-1-benzopyran-2,2′-[2H]indoles] to pyrrolo[1,2-a]indole derivatives

✍ Scribed by Vytas Martynaitis; Algirdas Šačkus; Ulf Berg

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
68 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Heating of 1′‐(N‐substituted carbamoyl)methylspiro[2__H__‐1‐benzopyran‐2,2′‐[2__H__]indoles] with potassium hydroxide in ethanol yields diastereomeric 5a,13‐methano‐6__H__‐1,3‐benzoxazepino[3,2‐a]indole‐12‐carbox‐amides. Reduction of the latter with sodium borohydride affords 1,2,3,9a‐tetrahydro‐2‐hydroxyaryl‐9__H__‐pyrrolo[ 1,2‐a] indole‐3 ‐carboxamides.

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