An unprecedented nitrogen elimination reaction: mechanistic studies using 15N-labeled 4-amino-7-benzylpyrrolo[2,3-d][1,2,3]triazine-5-carbonitrile.
An unprecedented nitrogen elimination reaction: mechanistic studies using 15N-labeled 4-amino-7-benzylpyrrolo[2,3-d][1,2,3]triazine-5-carbonitrile.
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前所未有的氮消除反应：使用 15N 标记的 4-氨基-7-苄基吡咯并[2,3-d][1,2,3]三嗪-5-甲腈进行机理研究。
DOI：
10.1021/ol990006x
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发表时间：
1999
期刊：
影响因子：
5.2
通讯作者：
Townsend,LB
中科院分区：
文献类型：
--
作者：
Migawa,MT;Townsend,LB
In the course of our work on novel pyrrolo[2,3-d][1,2,3]triazines we have discovered that1undergoes an elimination of nitrogen at 250 °C to give2. We have conducted15N labeling studies that establish that the loss of N-2 and N-3 from1had occurred rather than N-1 and N-2, presumably via a retro Diels−Alder reaction of the imino tautomer7. This study provides an alternative to the commonly accepted mechanism which involves the loss of N-1 and N-2 via the transient formation of a diazonium compound generated from 4-amino- or 4-oxo-substituted 1,2,3-triazines condensed with carbocycles or heterocycles.
