✦ LIBER ✦

Regioselective unusual formation of spirocyclic 4-{3′-benzo(2′,3′-dihydro)furo}-9-methyl-2,3,9-trihydrothiopyrano [2,3-b]indole by acid-catalyzed reaction of enol ethers

✍ Scribed by K. C. Majumdar; S. Alam; B. Chattopadhyay

Publisher: Journal of Heterocyclic Chemistry
Year: 2009
Tongue: English
Weight: 143 KB
Volume: 46
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.31

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✦ Synopsis

Abstract

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Spirocyclic 4‐{3′‐benzo(2′,3′‐dihydro)furo}‐9‐methyl‐2,3,9‐trihydrothiopyrano[2,3‐b]indoles are regioselectively synthesized by treating suitable enol ethers, 4‐aryloxymethylene‐9‐methyl‐2,3,9‐trihydrothio‐pyrano[2,3‐b]indoles with H~2~SO~4~ in dichloromethane‐methanol‐water. The substrates for the aforesaid reaction are in turn synthesized by the thio‐Claisen rearrangement of 2‐(4′‐aryloxybut‐2′‐ynylthio)‐1‐methylindoles. J. Heterocyclic Chem., 46, 62 (2009).

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