Pteridines. 49. Synthesis of 2,4-Diamino-6,8-dihydro-7-aryl-8-oxopyrrolopteridines

Article abstract of DOI:10.1021/jo00340a025

Reaction of ethyl 4-chloro-2-oximino-3-oxobutyrate (14) with aminomalononitrile tosylate followed by deoxygenation of the resulting pyrazine 1-oxide provides 2-amino-6-carbethoxy-5-(chloromethyl)-3-cyanopyrazine (11).Treatment of 11 with arylamines gives 2-amino-5-<(arylamino)methyl>-6-carbethoxy-3-cyanopyrazines (12) which are readily cyclized to 1,3-dihydro-1-oxopyrrolo<3,4-b>pyrazines (13).Condensation of 13 with guanidine acetate in dimethylformamide then provides the title compounds.