3,6-二(吡啶-2-基)-1,2,4,5-四嗪的合成及应用

Synthesis and application of 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine

以2-氰基吡啶和水合肼为原料,经过Pinner反应和氧化反应合成得到3,6-二(吡啶-2-基)-1,2,4,5-四嗪(化合物1),收率为88.6%。对影响产物收率的因素进行了考察,确定了第二步氧化反应的反应温度为0℃,反应时间1.0h。化合物1分别与6,7-二溴-1,4-二氢-1,4-环氧萘(化合物4a)和6,7-二甲氧基-1,4-二氢-1,4-环氧萘(化合物4b)反应得到5,6-二溴异苯并呋喃(化合物5a)和5,6-二甲氧基异苯并呋喃(化合物5b)的收率分别为51.3%和48.5%。化合物1和化合物5a以及化合物5b的结构均采用~1H-NMR和ESI-MS进行了表征。

3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine was synthesized from picolinonitrile and hydrazine hydrate by a two-step reaction of Pinner reaction and oxidation reaction in 88.6%yield.The optimal reaction conditions of second step were also investigated as follows:the reaction temperature is 0℃,the reaction time is 1.0 h.When 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine(1)reacted with 6,7-dibromo-1,4-dihydro-1,4-epoxynaphthalene(4 a)and 6,7-dimethoxy-1,4-dihydro-1,4-epoxynaphthalene(4 b)respectively,5,6-dibromoisobenzofuran(5 a)and 5,6-dimethoxyisobenzofuran(5 b)were obtained in 51.3%and 48.5%respectively.The structure of 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine(1),5,6-dibromoisobenzofuran(5 a)and 5,6-dimethoxyisobenzofuran(5 b)were confirmed by^1H-NMR and ESI-MS.