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Efficient Synthetic Approach to Substituted Benzo[ b ]furans and Benzo[ b ]thiophenes by Iodine‐Promoted Cyclization of Enaminones
Author(s) -
Labarrios Ehecatl,
Jerezano Alberto,
Jiménez Fabiola,
Carmen Cruz María,
Delgado Francisco,
Zepeda L. Gerardo,
Tamariz Joaquín
Publication year - 2014
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.1686
Subject(s) - chemistry , furan , thiophene , iodine , reactivity (psychology) , aryl , ring (chemistry) , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , alternative medicine , pathology , medicine , alkyl
An efficient synthetic approach to the substituted benzo[ b ]furan and benzo[ b ]thiophene scaffolds by iodine‐mediated cyclization of the corresponding enaminones is described. This protocol was applied to a large series of these latter precursors to afford the respective benzoheterocycles substituted at the C‐2 position by a carbonyl group functionality. A study of the factors that control this process reveals that the reactivity depends on the presence of electron‐donor groups in the aryl ring of the aryloxycarbonylic and arylthiocarbonylic moieties.