Synthesis and Reactions of 4 (3'4'5'6'-Tetrahalophthalyidene) -2-Aryl-5 (4)-Oxazolones

A. A. Afify¹, A. Y. Soli Man¹*, M. A. El-Hashash², G. H. Sayed² and M. M. Amer¹

¹Chemistry Department, Faculty of Science, Ain Shams University, ²Faculty of Teachers at El-Fayown, Cairo University, Cairo, Egypt

ABSTRACT:

4-(3',4',5',6'-Tetrahalophthalylidene)-2-aryl-5 (4 -oxazolone (I) was prepared. Hydrazinolysis of I gave the hydrazides (II). I_a Reacted with aniline in molar ratio (1:1) or (1:2) and yielded tet-rachlorophthaly idene N-phenyl hippuric acid amide (III) or a mixture of the imidazolones (IVa) and (V). AminoJysis of 1± with primary amines gave (III_b and _e ) and (IV_b ). Oxazolones (I) underwent ring opening reactions with cumene under Friedel Crafts conditions to give the phthalide derivative (VI). However, arylation of (I) with o-xylene yielded (VII) via hetero-ring opening follo¬wed by dearylation. While with m-xylene, compound (VIII) was obtained by ring opening with 1,4-arylation of the oxazolone (I_e).

KEYWORDS:

Reactions; (4)-Oxazolones

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Copy the following to cite this article: Afify A. A, Soli Man A. Y, El-Hashash M. A, Sayed G. H, Amer M. M. Synthesis and Reactions of 4 (3'4'5'6'-Tetrahalophthalyidene) -2-Aryl-5 (4)-Oxazolones. Orient J Chem 1987;3(1).

Copy the following to cite this URL: Afify A. A, Soli Man A. Y, El-Hashash M. A, Sayed G. H, Amer M. M. Synthesis and Reactions of 4 (3'4'5'6'-Tetrahalophthalyidene) -2-Aryl-5 (4)-Oxazolones. Orient J Chem 1987;3(1). Available from: http://www.orientjchem.org/?p=42210