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Regioselective synthesis of 4-aryloxymethylene-2,3,5-trihydrothiopyrano[3,2-b]indoles by the thio-claisen rearrangement of 3-(4′-aryloxybut-2′-ynylthio)indoles

✍ Scribed by K. C. Majumdar; S. Alam; S. Muhuri

Publisher: Journal of Heterocyclic Chemistry
Year: 2007
Tongue: English
Weight: 345 KB
Volume: 44
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570440624

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✦ Synopsis

Abstract

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A number of new 4‐aryloxymethylene‐2,3,5‐trihydrothiopyrano[3,2‐b]indoles are regioselectively synthesized in 78‐84% yield by the thio‐Claisen rearrangement of 3‐(4′‐aryloxybut‐2′‐ynylthio)indoles. The endocyclic double bonded products are isolated by introducing electron withdrawing acetyl group at the indole nitrogen and also can be converted to the corresponding exocyclic isomers by deacetylation and subsequent heating.

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