3-芳基-6-甲基-1,6-二氢-1,2,4,5-四嗪及其衍生物的合成和晶体结构

以乙腈和芳基腈为原料, 经过醚化、环化和还原三步方便且有效地合成了3-芳基-6-甲基-1,6-二氢-1,2,4,5-四嗪, 并在此基础上合成了一系列新的3-芳基-6-甲基-1,6-二氢-1,2,4,5-四嗪衍生物, 通过元素分析, ¹H NMR, IR和HRMS对这些化合物进行了表征. 对化合物N-邻甲基苯-3-苯基-6-甲基-1,6-二氢-1,2,4,5-四嗪-1-甲酰胺(5a)的X射线晶体衍射研究表明: 其属于单斜晶系, P2_{1 /c空间群, 晶胞参数a＝1.3941(6) nm, b＝0.5675(2) nm, c＝2.0614(8) nm; α＝γ＝90°, β＝102.055(6)°; V＝1.5949(11) nm³, 此类化合物的四嗪环采用不对称船式结构, 且具有同芳香性.}

Synthesis and Structures of 3-Aryl-6-methyl-1,6-dihydro-1,2,4,5-tetrazines and Their Derivatives

A convenient and effective method was developed from the starting materials acetonitrile and aryl nitrile via three steps to synthesize 3-aryl-6-methyl-1,6-dihydro-1,2,4,5-tetrazines. On the basis of which, some 3-aryl-6-methyl-1,6-dihydro-1,2,4,5-tetrazine derivatives were synthesized and characterized by elemental analysis,~1H NMR, IR and HRMS techniques. The X-ray single crystal diffraction study of 6-methyl-3-phenyl-N-(2-tolyl)-1,6-dihydro-1,2,4,5-tetrazine-1-carboxamide (5a) indicates that 5a belongs to a monoclinic system, with a=1.3941(6) nm, b=0.5675(2) nm, c=2.0614(8) nm; α=γ=90°, β=102.055(6)°; V= 1.5949(11) nm~3. The central tetrazine ring adopts an unsymmetrical boat structure. It could be considered that the molecule had a homoaromaticity.