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

作　　者：耿亮[1] 雷鸣[1] 王彦广[1] 

机构地区：[1]浙江大学化学系,杭州310027

出　　处：《有机化学》2005年第6期690-695,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20272051)资助项目.

摘　　要：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.A facile method for preparation of 5-methyl-5-[5-(tert-butyldimethylsiloxymethyl)-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 H-1 NMR, C-13 NMR, MS, IR and HRMS spectra.

关 键 词：噁唑 吡唑啉 噁二唑 Schiff碱 偶极环加成反应 唑类化合物 合成 甲氧基苯基 核磁共振谱 高分辨质谱 腈氧化物 原位生成 环化反应 取代苯肼 不饱和酮 新化合物 红外光谱 羟甲基 乙酰基 二甲基 叔丁基 一锅法 二芳基 吡唑基 

分 类 号：O626.1[理学—有机化学]