Synthesis of Diazanorcaradienes and 1,2‐Diazepines via the Tandem [4+2]‐Cycloaddition/Retro‐[4+2]‐Cycloaddition Reaction between Methoxycarbonylcyclopropenes and Dimethoxycarbonyltetrazine

Abstract

The reaction of di(methoxycarbonyl)tetrazine with substituted cycloprop‐2‐ene‐1‐carboxylates gives a series of 3,4‐diazanorcaradienes and 1,2‐diazepines. The influence of the nature of cyclopropenes and the reaction conditions on its selectivity was investigated. The addition of nucleophiles to norcaradienes was studied and a rare example of the “walk” rearrangement in this class of compounds was revealed.