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 | Zendy

Majumdar K. C. | Zendy; Alam S. | Zendy; Chattopadhyay B. | Zendy

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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).

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