Orthoamides and iminium salts LXXXII[1]. The cleavage of orthoamides of alkynecarboxylic acids by trimethylsilyl azide[Orthoamide und iminiumsalze, LXXXII[1]. Die spaltung von alkincarbons?ure-orthoamiden mit trimethylsilylazid]

摘要

The cleavage of orthoamides of alkynecarboxylic acids 5 with trimethylsilyl azide affords 4-[bis(dimethylamino)methylene]-4H-1, 2, 3-triazoles 9. By treatment of the bis-orthoamide of acetylenedicarboxylic acid 1 with trimethylsilyl azide and benzoyl azide, respectively, the 5-[bis(dimethylamino)methylene]-5H-1, 2, 3-triazole carboxamidinium salt 12a is accessible. Iminium salts 10 and 14 can be prepared by methylation of the triazoles 9 and 12a in 2-position of the triazole ring. The crystal structure of 5H-1, 2, 3-triazole-4- carboxamidinium tetraphenylborate 12b is reported.