1187086-07-2Relevant academic research and scientific papers
Reactions of 9-aryl-6-cyanopurines with primary amines
Al-Azmi, Amal,Anita Kumari
experimental part, p. 2245 - 2262 (2010/04/29)
Two structural isomers (9-aryl-6-cyanopurines and imidazole-4,5-dicarbonitriles) were isolated from the reaction of (Z)-N1-aryl-N2-(2-amino-1,2-dicyanovinyl)formamidines with triethyl orthoacetate or propionate. On the other hand, 9-aryl-6-cyanopurines were the only product, when triethyl orthoformate was used. The reaction of 9-aryl-6-cyanopurines with hydroxylamine hydrochloride in dichloromethane/ethanol at room temperature furnished 6-amidinopurines, while reaction with primary amines afforded pyrimido[5,4-d]pyrimidines. In addition, 9-aryl-6-cyanopurines reacted with hydrazine monohydrate under mild conditions to give 4-imino-N8-arylpyrimido[5,4-d]pyrimidines. The latter furnished novel pyrimido[4,5-e][l,2,4]triazolo[l,5-c]pyrimidines when refluxed with an excess of triethyl orthoesters. The new compounds were fully characterized and single crystal X-ray analyses have been carried out on 9-(4-methoxyphenyl)-9H-purine-6-carboximidamide and 2-methyl-1-[(E)-p-tolyliminomethyl]-1H-imidazole-4,5-dicarbonitrile.
