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

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

Volume: 3 Issue: 3

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

Affiliation:

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

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.

Cite this article as:

Majumdar C. Krishna, Alam Safiul and Muhuri Sanjukta, Regioselective Synthesis of Thieno[3,2-β]Indole by Tandem Cyclization of 1-Acetyl-3-(4-Aryloxybut-2-Ynylthio)Indole (Experimental Section), Letters in Organic Chemistry 2006; 3 (3) . https://dx.doi.org/10.2174/157017806775789868