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Abstract s In this work, efforts have been directed toward developing new synthetic routes for synthesis of 4-substituted-2-phenyl oxazolones as precursors to variety of azole and azine derivatives of expected biological activities. The newly synthesized derivatives were obtained on subjecting the 5-oxzaolones to ring transformation under varieties of reagents and reaction conditions which could effect their rearrangements. A new facial route for synthesis of 4-arylideneoxazolones 2a-m is presented. In this methodology, arylmethylene malononitriles 1 were utilized as a trans-arylidene reagent on their reaction with hippuric acid. The reaction sequence takes place via Tandem Michael addition/retro Michael reaction with extrusion of malononitrile. The procedure constitutes a general fashion since the reaction was amenable to a variety of ylidene malononitriles extended from that derived from aromatic aldehydes to that derived from acyclic and cyclic ketones and ketoesters. |