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Synthesis and reactivity of 6‐methyl‐4 H ‐furo[3,2 c ]pyran‐3,4‐dione
Author(s) -
HikemOukacha Djamila,
Rachedi Yahïa,
Hamdi Maamar,
Silva Artur M.S.
Publication year - 2011
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.490
Subject(s) - chemistry , pyran , dehydroacetic acid , thiourea , acetic acid , halogenation , reactivity (psychology) , organic chemistry , medicinal chemistry , medicine , alternative medicine , pathology
An efficient synthesis of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one by bromination of dehydroacetic acid in glacial acetic acid is described. Novel 4‐hydroxy‐6‐methyl‐3‐(2‐substituted‐thiazol‐4‐yl)‐2 H ‐pyran‐2‐ones have been prepared from the reaction of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one with thioamides, thiourea, and diphenylthiocarbazone. The condensation reaction of 6‐methyl‐4 H ‐furo[3,2 c ]pyran‐3,4‐dione, obtained from the reaction of 3‐bromoacetyl‐4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one with aliphatic amines, with benzaldehydes and acetophenones led to novel 2‐arylidene‐6‐methyl‐2 H ‐furo[3,2‐ c ]pyran‐3,4‐diones and 6‐(2‐arylprop‐1‐enyl)‐2 H ‐furo[3,2‐ c ]pyran‐3,4‐diones. The structure of all compounds was established by elemental analysis, IR, NMR, and mass spectra. J. Heterocyclic Chem., 2011.