Regioselective Synthesis of Thieno[3,2-β]Indole by Tandem Cyclization of 1-Acetyl-3-(4'-Aryloxybut-2'-Ynylthio)Indole (Experimental Section)

Authors: Majumdar, Krishna C.; Alam, Safiul; Muhuri, Sanjukta

Source: Letters in Organic Chemistry, Volume 3, Number 3, March 2006 , pp. 250-252(3)

Publisher: Bentham Science Publishers

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Abstract:

A number of thieno[3,2-b]indoles have been regioselectively synthesized in 85-90% yield by the tandem cyclization of 1-acetyl-3-(4'-aryloxybut-2'-ynylthio)indoles on treatment with one equivalent of m- CPBA in CH2Cl2 at rt for 1 h. 1-Acetyl-3-(4'-aryloxybut-2'-ynylthio)indoles were in turn prepared from indole via (i) formation of thiuronium salt (ii) then reacting with 1-aryloxy-4-chlorobut-2-yne (iii) acetylation with acetyl chloride under PTC condition.

Keywords: Sulfoxide rearrangement; thieno[3,2-b]indole; [2,3]sigmatropic rearrangement; [3,3]sigmatropic rearrangement; regioselective synthesis; m-CPBA

Document Type: Research article

DOI: http://dx.doi.org/10.2174/157017806775789868

Affiliations: 1: Department of Chemistry, University of Kalyani, Kalyani 741 235, W.B., India.

Publication date: 2006-03-01

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