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Synthesis of 4‐Oxo‐3a,4,5,6‐tetrahydroimidazo[1,5‐b]isoxazole‐3‐carboxylic Acid Esters

Authors :
Bilal Yilmaz
Necdet Coşkun
Uludağ Üniversitesi/Fen-Edebiyat Fakültesi/Kimya Bölümü.
Coşkun, Necdet
Yılmaz, Bilal
Source :
Synthetic Communications. 34:1617-1623
Publication Year :
2004
Publisher :
Informa UK Limited, 2004.

Abstract

3‐Imidazoline 3‐oxides react regioselectively with 3‐phenylpropanoic acid alkyl esters to give the corresponding 2‐phenyl‐3a,4,5,6‐tetrahydroimidazo[1,5‐b]isoxazole‐3‐carboxylic acid alkyl esters. This adducts convert to imidazole and the corresponding alkyl 3‐oxo‐3‐phenylpropanoic acid esters when treated with alkoxides or heated under vacuum. Attempts to oxidise the carbon–carbon double bond using KMnO4–FeSO4 led to the formation of heretofore unknown 4‐oxo‐3a,4,5,6‐tetrahydroimidazo[1,5‐b]isoxazoles.

Details

ISSN :
15322432 and 00397911
Volume :
34
Database :
OpenAIRE
Journal :
Synthetic Communications
Accession number :
edsair.doi.dedup.....b8ce6e3b4c83ef663eb5672bc16d3bcb