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Synthesis and characterization of new α,β‐unsaturated γ‐lactones: Alkyl 3‐acetyl‐4‐hydroxy‐2‐methyl‐5‐oxo‐2,5‐dihydrofuran‐2‐ylcarbamates
Author(s) -
Üngören Ş. H.,
Saçmaci M.,
Akçamur Y.,
Arici C.,
Ülkü D.
Publication year - 2005
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.5570420431
Subject(s) - chemistry , tautomer , enol , alkyl , carbamate , proton nmr , organic chemistry , stereochemistry , catalysis
Abstract A convenient procedure for the preparation of carbamate derivatives of 5‐oxo‐2,5‐dihydrofuran ( 3 ) was described. The method is based on the Michael type addition of three alkyl carbamates ( 2 ) with 4‐acetyl‐5‐methyl‐2,3‐dihydro‐2,3‐furandione ( 1 ). According to 1 H nmr spectra of compounds show tautomeric forms ( 3,4,5 ) in CDC1 3 . In the solid state the synthesized compounds are enol forms ( 3 ). The products were characterized with molecular spectroscopic methods.