1,3-Dipolar Cycloaddition of Carbodiimides and Nitrilimines: Synthesis and Mechanistic Study of 5-Amino-1,2,4-triazoles
作者:Wan-Ping Yen、Fung-Chun Kung、Fung Fuh Wong
DOI:10.1002/ejoc.201600240
日期:2016.5
An effective 1,3-dipolar cycloaddition was developed for the synthesis of 5-amino-1,2,4-triazoles by reacting hydrazonoyl hydrochlorides (nitrilimines) with carbodiimides in the presence of triethylamine as a base. Both symmetric and asymmetric carbodiimides are compatible with this newly developed reaction; diphenyl carbodiimide is the one exception. Mechanistic studies indicate that alkyl and cycloalkyl
开发了一种有效的 1,3-偶极环加成反应,通过在三乙胺作为碱的存在下使腙酰盐酸盐(腈亚胺)与碳二亚胺反应来合成 5-氨基-1,2,4-三唑。对称和不对称碳二亚胺都与这种新开发的反应相容;二苯基碳二亚胺是一个例外。机理研究表明,1,2,4-三唑环上季 N+-R 的烷基和环烷基部分作为潜在的离去基团,可以有效地脱离中间体 4,5-二氢-4-烷基-5-亚氨基- 1,2,4-三唑。