A. Albert
1986
Citations
0
Influential Citations
9
Citations
Journal
Advances in Heterocyclic Chemistry
Abstract
Publisher Summary This chapter provides a brief description of 4-Amino-1,2,3-triazoles. The 4-aminotriazoles are of special interest because of their properties. The amino group attenuates, by electronic release, the normally π-deficient character of the triazole nucleus. A strong bathochromic shift in the UV spectrum is evident. This 4-amino group introduces the possibility for ring opening, followed by the closure to isomers, often 4-alkylaminotriazoles that would be difficult otherwise to synthesize. This process, known as the Dimroth rearrangement, can advantageously be reversed to avoid the use of dangerous reagent methyl azide. In combination with a suitable group in 5 position, the 4-amino group permits annelation of a new ring on to the triazole ring. It is exceedingly useful to be able to make any 4,5-disubstituted triazole required for generating such bicyclic systems. 4-Amino-1,2,3-triazole analogs of 4-aminoimidazole-5-carboxamide that is a necessary intermediate for the synthesis of purines in all forms of life have proved to be valuable inhibitors in experimental biology.