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Regioselective unusual formation of spirocyclic 4‐{3′‐benzo(2′,3′‐dihydro)furo}‐9‐methyl‐2,3,9‐trihydrothiopyrano [2,3‐ b ]indole by acid‐catalyzed reaction of enol ethers
Author(s) -
Majumdar K. C.,
Alam S.,
Chattopadhyay B.
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.31
Subject(s) - chemistry , enol , indole test , regioselectivity , methanol , dichloromethane , catalysis , thio , claisen rearrangement , enol ether , medicinal chemistry , stereochemistry , organic chemistry , solvent
pirocyclic 4‐{3′‐benzo(2′,3′‐dihydro)furo}‐9‐methyl‐2,3,9‐trihydrothiopyrano[2,3‐ b ]indoles are regioselectively synthesized by treating suitable enol ethers, 4‐aryloxymethylene‐9‐methyl‐2,3,9‐trihydrothio‐pyrano[2,3‐ b ]indoles with H 2 SO 4 in dichloromethane‐methanol‐water. The substrates for the aforesaid reaction are in turn synthesized by the thio ‐Claisen rearrangement of 2‐(4′‐aryloxybut‐2′‐ynylthio)‐1‐methylindoles. J. Heterocyclic Chem., 46 , 62 (2009).