144486-68-0Relevant academic research and scientific papers
Synthesis of new imidazo[4,5-d][1,3]diazepine derivatives from 5-amino-4-(cyanoformimidoyl)imidazoles
Dias, Alice W.,Proenca, M. Fernanda J. R. P.,Booth, Brian L.
, p. 855 - 862 (1996)
N1-[(Z)-2-Amino-1,2-dicyanovinyl]formamidines 1a-d react readily with tosyl isocyanate to form novel 8-amino-3-substituted-5-oxo-7-tosylaminoimidazo[4,5-d][1,3]diazepines 6a-d rather than the 6-cyano-2-oxopurine derivatives 5a-d expected. Compound 5a has been synthesized from 1a by reaction with ethyl chloroformate and base-catalyzed cyclization of the resultant 5-ethoxycarbonylamino-4-(cyanoformimidoyl)imidazole. Treatment of the 5-amino-4-cyanoimidazoles 7a and b with tosyl isocyanate under similar conditions gives the 4-cyano-5-(3′-tosylureido)imidazoles 8a and b, which on treatment with ethanolic ammonia cyclizes to the corresponding isoguanines 10a and b.
Synthesis of 9-Hydroxyalkyl-substituted Purines from the Corresponding 4-(C-Cyanoformimidoyl)imidazole-5-amines
Booth, Brian L.,Dias, Alice M.,Proenca, M. Fernanda
, p. 2119 - 2126 (2007/10/02)
The amino alcohols HO(CH2)nNH2 (n = 2, 3 and 5) react readily with ethyl (Z)-N-(2-amino-1,2-dicyanovinyl)formimidate 5 to give the amidines 6a-c, which cyclize in the presence of DBU (1,8-diazabicycloundec-7-ene) to give the corresponding 4-(cyanoformimidoyl)imidazole-5-amines 7a-c, which can be isolated in the cases where n = 2 or 3. In the presence of aldehydes and ketones, the imidazoles 7a-d lead to the 6-carbamoyl-1,2-dihydropurines 9a-f which, in some cases, are oxidised to the corresponding 6-carbamoylpurines.The reaction of the imidate 5 with 2-methoxyethylamine leads to the amidine 6d and, on treatment with DBU, the reactive imidazole 7d which can be used directly for further reaction.
