Volume 18, Issue 38
Heterocyclic Compounds
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ChemInform Abstract: Cyclization of C- and O-Acyl Derivatives of p-Toluamide O-Acetoacetyloxime.

E. KAWASHIMA

E. KAWASHIMA

Dep. Org. Chem., Tokyo Coll. Pharm., Hachioji City, Tokyo 192-03, Japan

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Y. ANDO

Y. ANDO

Dep. Org. Chem., Tokyo Coll. Pharm., Hachioji City, Tokyo 192-03, Japan

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K. TABEI

K. TABEI

Dep. Org. Chem., Tokyo Coll. Pharm., Hachioji City, Tokyo 192-03, Japan

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H. MIYAMAE

H. MIYAMAE

Dep. Org. Chem., Tokyo Coll. Pharm., Hachioji City, Tokyo 192-03, Japan

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First published: September 22, 1987

Abstract

The O-acyl or C-acyl derivatives (III) and (IV) of the ketone (I) are cyclized, yielding the oxadiazoles (VI) and (VII) or the oxadiazoles (VII), (VIII), (X), and (XI), together with the isoxazolinone (IX).

ChemInform Abstract

The O-acyl or C-acyl derivatives (III) and (IV) of the ketone (I) are cyclized, yielding the oxadiazoles (VI) and (VII) or the oxadiazoles (VII), (VIII), (X), and (XI), together with the isoxazolinone (IX). Acylation of (I) with the acid chlorides (II) gives the compounds (V) as by-products. Acylation of the aminomethyleneisoxazolinone (IX) forms the carboxamides (XIV). (Intermediates, mechanism,crystal data of (XIVb): space group P21/c, Z=4).

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