Orthoamide und Iminiumsalze, LXXXII [1]. Die Spaltung von Alkincarbonsäure-orthoamiden mit Trimethylsilylazid / Orthoamides and Iminium Salts LXXXII [1]. The Cleavage of Orthoamides of Alkynecarboxylic Acids by Trimethylsilyl Azide

Abstract

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