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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (06): 690-695. 上一篇    下一篇

研究论文

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*   

  1. (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*   

  1. (Department of Chemistry, Zhejiang University, Hangzhou 310027)
  • Received:2004-07-05 Revised:2004-12-27 Published:2005-05-30
  • Contact: WANG Yan-Guang

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1813

被引次数

21 | 4

通过3-乙酰基-5-羟甲基异噁唑衍生的Schiff碱2与由醛肟原位生成的腈氧化物的1,3-偶极环加成反应, “一锅法”制备了5-甲基-5-[5-(叔丁基二甲基硅氧基甲基)-3-异噁唑基]-3-芳基-4-(4-甲氧基苯基)-4,5二氢-1,2,4-噁二唑类化合物4a～4e; 同时由3-乙酰基-5-羟甲基异噁唑衍生的α,β-不饱和酮(5)与取代苯肼的环化反应制备了5-(叔丁基二甲基硅氧基甲基)-3-[(1,5-二芳基)-3-(4,5-二氢吡唑基)]-异噁唑类化合物6a～6i. 所有新化合物的结构经核磁共振谱氢谱和碳谱、质谱、红外光谱以及高分辨质谱等进行了确证.

关键词: 1,3-偶极环加成, 腈氧化物, 1,2,4-噁二唑啉, 吡唑啉

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