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四嗪

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1,2,3,4-四嗪
1,2,3,4-四嗪
1,2,4,5-四嗪
1,2,4,5-四嗪

四嗪(Tetrazine)是含有四个原子的六元杂环化合物,不稳定,分子式为C2H2N4。理论上它有三种异构体:1,2,3,4-四嗪、1,2,4,5-四嗪、1,2,3,5-四嗪,但只有前两种是已知的。1,2,3,4-四嗪不稳定,常以与其他芳香环稠合及双N-氧化物的形式存在。

1,2,4,5-四嗪

1,2,4,5-四嗪是已知的,很多3,6-二取代-1,2,4,5-四嗪都已制得,并且研究得很广泛。它们中,有些可以用作能量材料。重氮乙酸乙酯在强碱存在下生成1,2,4,5-四嗪-3,6-二羧酸,再经脱羧便得到1,2,4,5-四嗪。阴极电解还原时,1,2,4,5-四嗪可以生成一个阴离子自由基,其中的负电荷几乎全部离域在氮原子上。

亚氨醚的盐与在低温下作用是制取3,6-二取代-1,2,4,5-四嗪类化合物的通用方法:[1]

用亚氨醚的盐与肼低温反应制取3,6-二取代-1,2,4,5-四嗪类化合物

此类化合物可用作制取多种化合物的前体,包括哒嗪类、𫫇二唑类及二苄叉肼等。当与降冰片二烯乙炔发生Diels-Alder反应时,它放出一分子氮气,生成哒嗪类化合物,见下图。[2]

降冰片二烯与1,2,4,5-二嗪衍生物发生DA反应

参见

参考资料

  1. ^ 陈敏为、甘礼骓.《有机杂环化合物》(第一版).北京:高等教育出版社,1990年6月.页222.ISBN 7-04-001122-0
  2. ^ π-Bond Screening in Benzonorbornadienes: The Role of 7-Substituents in Governing the Facial Selectivity for the Diels-Alder Reaction of Benzonorbornadienes with 3,6-Di(2-pyridyl)-s-Tetrazine. Ronald N. Warrener and Peter A. Harrison Molecules 2001, 6, 353–369. 文献链接页面存档备份,存于互联网档案馆
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四嗪
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