Title of article :
Regioselective Synthesis of Thieno[3,2-b]Indole by Tandem Cyclization of 1-Acetyl-3-(4 -Aryloxybut-2 -Ynylthio)Indole
Author/Authors :
Majumdar, Krishna C. University of Kalyani - Department of Chemistry, India , Alam, Safiul University of Kalyani - Department of Chemistry, India , Muhuri, Sanjukta University of Kalyani - Department of Chemistry, India
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 indolevia (i) formation of thiuronium salt (ii) then reacting with 1-aryloxy-4-chlorobut-2-yne (iii) acetylation withacetyl chloride under PTC condition.
Keywords :
Sulfoxide rearrangement , thieno[3 , 2 , b]indole , [2 , 3]sigmatropic rearrangement , [3 , 3]sigmatropic rearrangement , regioselective synthesis , m , CPBA
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
