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A New Approach to the Synthesis of N , N ‐Dialkyladenine Derivatives
Author(s) -
Alves M. José,
Carvalho M. Alice,
Carvalho Sílvia,
Dias Alice M.,
Fernandes Francisco H.,
Proença M. Fernanda
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700416
Subject(s) - chemistry , acetal , dimethylformamide , amine gas treating , purine , medicinal chemistry , stereochemistry , organic chemistry , solvent , enzyme
N , N‐ Dialkyladenine derivatives were prepared by two different reaction sequences starting from 5‐amino‐4‐cyanoformimidoylimidazoles. When these imidazoles were treated with dimethylformamide diethyl acetal, a 5‐aminomethyleneamino‐4‐cyanoformimidoylimidazole was isolated and evolved to the N , N‐ dialkyladenine in the presence of a secondary alkylamine. The same purine structure was isolated when the 5‐amino‐4‐cyanoformimidoylimidazole was first treated with a secondary amine to give a stable 4‐amidino‐5‐aminoimidazole. The desired product was generated when the 4‐amidino‐5‐aminoimidazole was combined with dimethylformamide diethyl acetal, at room temperature. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)