The preparation of both 1-and 3-deaza-8-azapurine (5-triaeolopyridines) analogs of adenine, purine-6 (1H)-thione, 6-(methylthio) purine, and hypoxanthine are reported. The Dimroth rearrangement of the 7-amino-3H-v-triazolo [4, 5-b] pyridine (2)-4-amino-lH-v- triazolo [4, 5-c] pyridine (5) system and the rearrangement of two v-triazolopyridinethione- amino [1, 2, 3] thiadiazolopyridine systems are described.