A novel and one pot synthesis of ethyl 7,12-dihydro-1,3,6,7,12-pentaazapleiadene5-carboxylates

Department of Discovery Chemistry, Aurigene Discovery Technologies Ltd., Hyderabad-500 049,

Telangana, India

E-mail : vijay_p@aurigene.com, potluri.vijay@gmail.com

JNT University, Kukatpally, Hyderabad-500 072, Telangana, India

new tandem three-step synthesis of ethyl 7,12-dihydro-1,3,6,7,12-pentaazapleiadene-5-carboxylate derivatives (9a-j) has been accomplished stepwise. Reaction of 4-chloro-6-methylpyrimidine-5-carbonitrile with various 4- substituted 2-nitrobenzeneamines yielded the corresponding 4-(2-nitrophenylamino)-6-methylpyrimidine-5-carbonitriles (7aj). These phenylamino methylpyrimidines reacted with diethyl oxalate to furnish (Z)-ethyl 3-(6-(2-nitrophenylamino)-5- cyanopyrimidin-4-yl)-2-hydroxyacrylates (8a-j). The resulting (Z)-ethyl 3-(6-(2-nitrophenylamino)-5-cyanopyrimidin-4-yl)- 2-hydroxyacrylates on reduction with SnCl₂ .2H₂O in ethanol underwent cyclization to afford the desired products in good to very good yields.