AN IMPROVED SYNTHESIS OF 3,6-DIAMINO-1,2,4,5-TETRAZINE .2. FROM TRIAMINOGUANIDINE AND 2,4-PENTANEDIONE

被引：140

作者：

COBURN, MD

BUNTAIN, GA

HARRIS, BW

HISKEY, MA

LEE, KY

OTT, DG

机构：

[1] University of California, Los Alamos National Laboratory, Los Alamos, New Mexico

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 08期

关键词：

D O I：

10.1002/jhet.5570280844

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis for the title compound that gives an 80% overall yield was developed. Treatment of triaminoguanidine monohydrochloride (1) with 2,4-pentanedione (2) gave 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,2-dihydro-1,2,4,5-tetrazine (3) in 80-85% yield. Oxidation of 3 with nitric oxide or nitrogen dioxide to 3,6-bis(3,5-dimethyylpyrazol-1-yl)-1,2,4,5-tetrazine (4) followed by ammonolysis of 4 gave 3,6-diamino-1,2,4,5-tetrazine (5) in guantitatively yields.

引用

页码：2049 / 2050

页数：2