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Synthesis of 5-Amino-4-(cyanoformimidoyl)-1H-imidazole: a Reactive Intermediate for the Synthesis of 6-Carbamoyl-1,2-dihydropurines and 6-Carbamoylpurines

DOI: 10.1039/P19900001705

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1705 - 1712 (1990)

Update date:2022-08-05

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Authors:

Alves, M. JoseAlves, M. Jose

Booth, Brian L.Booth, Brian L.

Proenc, M. Fernanda J. R. P.Proenc, M. Fernanda J. R. P.

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Article abstract of DOI:10.1039/P19900001705

5-Amino-4-(cyanoformimidoyl)-1H-imidazole (3) has been prepared in good yield by the basecatalysed cyclisation of (Z)-N-(2-amino-1,2-dicyanovinyl)formamidine.Compound (3) reacts with ketones, R1COR2 to give 2,2-disubstituted-6-carbamoyl-1,2-dihydropurines as the major products, together with minor amounts of compounds believed to be novel 7-amino-1-carbamoyl-3,3-disubstituted 3H-imidazo<1,5-c>imidazole derivatives, which have been isolated when R1= R2= Et, Bu, and PhCH2; when R1= R2= Ph the only product isolated is tentatively assigned the imidazo<1,5-c>imidazole structure.In the reaction with acetylacetone the 1,2-dihydropurine intermediate is unstable and loses acetone to give 2-methyl-6-carbamoylpurine.The aldehydes RCHO also react readily with (3) at room temperature to give the corresponding 6-carbamoyl-1,2-dihydropurine derivatives, which can be isolated when R= Me or Et; these oxidise in solution to afford the corresponding 6-carbamoylpurines.

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Product name:2-benzyl-6-carbamoylpurine

Cas No:129694-58-2

129694-58-2

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