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Letters in Organic Chemistry

Author(s): Krishna C. Majumdar, Safiul Alam and Sanjukta Muhuri

DOI: 10.2174/157017806775789868

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

Page: [250 - 252] Pages: 3

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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