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A base-catalyzed cascade route to phenolic 6-cyanopurines via O -alkylformamidoximes

Abstract:

N-[1,2-Dicyano-2-(hydroxyphenylideneamino)vinyl]-O-alkylformamidoximes were prepared from the reaction of N-(2-amino-1,2-dicyanovinyl)-O-alkylformamidoximes with phenolic aldehydes. These compounds generated 2-hydroxyphenyl-4,5-dicyano-N-(N'-alkoxyformimidoyl)imidazoles in the presence of manganese oxide, whereas in triethylamine 6-cyano-8-hydroxy-phenylpurines were isolated. The reaction was followed by 1H NMR spectroscopy and a plausible mechanism is presented.