Abstract
The substitution reaction of 7-chloro-(1) and 7-(p-tolylsulfonyl)-3-phenyl-3H-1, 2, 3-triazolo [4, 5-d] pyrimidines (2) with various nucleophiles (NuH or Nu-) was carried out. The reaction of 1 with amines (NuH-1 to NuH-11) gave 7-(N-substituted amino)-3-phenyl-3H-1, 2, 3-triazolo [4, 5-d] pyrimidines (3-1 to 3-11). The reaction with alkoxide ions (Nu--12 to Nu--17) resulted in the formation of 7-alkoxy-3-phenyl-3H-1, 2, 3-triazolo-[4, 5-d] pyrimidines (3-12 to 3-17). Moreover, 1 reacted with carbanions which were formed by the reaction of active methylene compounds (NuH-19 to NuH-24) with sodium hydride, resulting in the introduction of a carbon chain into the 7-position of 1 (yielding 7-substituted 3-phenyl-3H-1, 2, 3-triazolo [4, 5-d] pyrimidines, 3-19 to 3-24). Similarly, the p-tolylsulfonyl group of 2 was easily displaced by nucleophiles (NuH-1 to NuH-24) to give the corresponding 7-substituted 3-phenyl-3H-1, 2, 3-triazolo [4, 5-d]-pyrimidines (3-1 to 3-24). The tautomerism of 7-substituted 3-phenyl-3H-1, 2, 3-triazolo [4, 5-d] pyrimidines (3-19 to 3-24) formed by the reaction with carbanions is discussed.
