2-异噁唑啉等氮杂环化合物在二铬酸氢四吡啶合镍(II)氧化下的脱氢芳构化反应  

Aromatization of 2-Isoxazolines and Some N-Containing Heterocyclic Compounds by Tetrakis-pyridine Nickel(II) Dichromate

作　　者：王炳祥[1] 何婷[2] 李邨[1] 胡宏纹[2] 

机构地区：[1]南京师范大学化学与环境科学学院,南京210097 [2]南京大学化学与化工学院,南京210093

出　　处：《有机化学》2003年第8期794-798,共5页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金 (No.2 0 0 72 0 1 6);江苏省教育厅自然科学基金 (No.0 0KJD1 50 0D1 );南京师范大学环境友好化学重点实验室资助项目

摘　　要：研究了 3 ,5 二芳基 4,5 二氢异唑化合物 ( 1a～ 1e) ,1,4 二氢吡啶化合物 ( 3a～ 3c)和 1,3 ,5 三苯基 4,5 二氢吡唑化合物 ( 5 )分别在二铬酸氢四吡啶合镍 (II) [(Py) 4 Ni(HCrO4) 2 ]氧化下脱氢反应的结果 ;研究了在 [(Py) 4 Ni(HCrO4) 2 ]存在下 ,吡啶叶立德、喹啉叶立德或异喹啉叶立德分别和缺电子烯烃反应 ,一步法合成中氮茚衍生物 9a～ 9b ,11a～ 11b ,13的结果 .发现金属配合物氧化剂二铬酸氢四吡啶合镍 (II)可用于多类杂环化合物的脱氢芳构化 .Aromatization of 3,5-diaryl-4,5-dihydroisoxazoles (1a～1e), 1,4-dihydropyridines (3a～3c) and 1,3,5-triphenyl-4,5-dihydropyrazole (5) were promoted by tetrakis-pyridine nickel(II) dichromate to yield the corresponding 3,5-diarylisoxazoles (2a～2e) in moderate yields (52%～72%), pyridine derivatives (4a～4b) in moderate to high yields (79%～88%) and 1,3,5-triphenylpyrazole (6) in 81% yield, respectively. A one-pot procedure was developed to prepare the derivatives of indolizines 9a～9b, 11a～11b and 13 in moderate to high yields (84%～93%) by the reaction of pyridinium N-ylides, isoquinolinium N-ylides or quinolinium N-ylides with electron-deficient 8a～8b in the presence of tetrakispyridine nickel(II) dichromate (TPND). The results showed that TPND possesses very good activities on the aromatization of N-containing heterocyclic compounds.

关 键 词：2-异噁唑啉 氮杂环化合物 二铬酸氢四吡啶合镍(Ⅱ) 氧化反应 脱氢芳构化 1 4-二氢吡啶 4 5-二氢异噶唑 4 5-二氢吡唑 

分 类 号：O626[理学—有机化学]