Journal of the Chemical Society. Perkin transactions I p. 913 - 917 (1992)
Update date:2022-08-05
Topics:
Alves, M. Jose
Booth, Brian L.
Freitas, A. Paula
Proenca, M. Fernanda J. R. P.
The reaction of ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formimidate with hydrazine monohydrate leads to (Z)-N3-(2-amino-1,2-dicyanovinyl)formamidrazone in almost quantitative yield.This compound proved to be an important starting material for the synthesis of the corresponding N1-isopropylidene- and N1-acetyl-formamidrazones.The amidrazones prepared promptly cyclize in the presence of base to give a 1,5-diamino-4-cyanoimidazole or a 1,5-diamino-4-(cyanoformimidoyl)imidazole, depending on the reaction conditions and mainly on the nature of the base used to induce cyclization. 1,5-Diamino-4-(cyanoformimidoyl)imidazole was treated with carbonyl compounds and the 1,2-dihydropurines thus isolated indicated that the amino group in position 5 is more reactive than that in position 1.
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