Synthesis of Isoxazolyl Substituted 1,2,4-Oxadiazolines and Pyrazolines

Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (06): 690-695. Previous Articles Next Articles

Original Articles

异噁唑基取代的1,2,4-噁二唑啉和吡唑啉类化合物的合成

耿亮，雷鸣，王彦广*

(浙江大学化学系杭州 310027)

收稿日期:2004-07-05 修回日期:2004-12-27 发布日期:2005-05-30
通讯作者: 王彦广

Synthesis of Isoxazolyl Substituted 1,2,4-Oxadiazolines and Pyrazolines

GENG Liang, LEI Ming, WANG Yan-Guang*

(Department of Chemistry, Zhejiang University, Hangzhou 310027)

Received:2004-07-05 Revised:2004-12-27 Published:2005-05-30
Contact: WANG Yan-Guang

Abstract

A facile method for preparation of 5-methyl-5-[5-(tert-butyldimethylsiloxy-methyl)-3-isoxazolyl]-3-aryl-4-(4-methyloxyphenyl)-4,5-dihydro-1,2,4-oxadiazoles (4a～4e) via 1,3-dipolar cycloaddition of Schiff bases derived from 3-acetyl-5-hydroxymethylisoxazoles and nitrile oxides in situ generated from oximes was described. 5-(tert-Butyldimethylsiloxymethyl)-3-(1,5-diaryl-4,5-dihydropyrazol-3-yl)isoxazoles (6a～6i) were also prepared through cycloaddition of aryl hydrazine and α,β-unsaturated ketones (5) derived from 3-acetyl-5-hydroxylmethylisoxazoles. The structures of all new compounds were characterized by ¹H NMR, ¹³C NMR, MS, IR and HRMS spec-tra.

Key words: 1,2,4-oxadiazoline, pyrazoline, nitrile oxide, 1,3-dipolar cycloaddition

Cite this article

GENG Liang, LEI Ming, WANG Yan-Guang*. Synthesis of Isoxazolyl Substituted 1,2,4-Oxadiazolines and Pyrazolines[J]. Chin. J. Org. Chem., 2005, 25(06): 690-695.

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异噁唑基取代的1,2,4-噁二唑啉和吡唑啉类化合物的合成

Synthesis of Isoxazolyl Substituted 1,2,4-Oxadiazolines and Pyrazolines

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