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(Z)-N3-(2-Amino-1,2-dicyanovinyl)formamidrazone: a Precursor in the Synthesis of 1,5-Diaminoimidazoles and 6-Carbamoyl-1,2-dihydropurines

DOI: 10.1039/P19920000913

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 913 - 917 (1992)

Update date:2022-08-05

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Authors:

Alves, M. JoseAlves, M. Jose

Booth, Brian L.Booth, Brian L.

Freitas, A. PaulaFreitas, A. Paula

Proenca, M. Fernanda J. R. P.Proenca, M. Fernanda J. R. P.

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Article abstract of DOI:10.1039/P19920000913

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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Product name:(Z)-N1-acetyl-N3-(2-amino-1,2-dicyanovinyl)formamidrazone

Cas No:141563-16-8

141563-16-8

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