74136-41-7

Upstream product

• 74414-82-7 3-Phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine-7-carbonitrile 
• 100-44-7 benzyl chloride 
• 99934-01-7 Phenyl-(3-phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-methanone 

Relevant academic research and scientific papers

Carbon-carbon bond cleavage of α-hydroxybenzylheteroarenes catalyzed by cyanide ion: Retro-benzoin condensation affords ketones and heteroarenes and benzyl migration affords benzylheteroarenes and arenecarbaldehydes

4-(α-Benzylα-hydroxybenzyl)quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4, 9, 12, 16-19) having an α-hydroxybenzyl group at the α-position of the nitrogen underwent retro-benzoin type condensation to afford kelones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13, 14, 15) having an α-benzyl-α-hydroxybelzyl group resulted in benzyl migration, giving benzylpyrazolopyrimidines (8) and arenecarbaldehydes (3). Tetrabutylammonium cyanide (11, Bu4NCN) was a more effective cyanide ion donor than KCN (10). The retro-benzoin condensation was applied to the synthesis of 2-substituted quinazolines (38) from 2-chloro-4- aroylquinazolines (34), using the aroyl group as a protecting and electron- withdrawing group.

Triazolopyrimidines. VI. 3-Phenyl-3H-1,2,3-triazolopyrimidine-7-carbonitrile and Related Compounds

Nucleophilic reagents were found to react with 3-phenyl-3H-1,2,3-triazolopyrimidine-7-carbonitrile (1) in two ways, depending on the nature of the reagent.One is substitution by attack of the reagent on the carbon at the 7-position, to which the cy