94453-57-3Relevant academic research and scientific papers
Synthesis of Compounds Related to 4(5)-Aminoimidazole-5(4)-carboxamides: Part VI - Synthesis of 3-(6-Methoxy-8-quinolyl)-7-methylpurin-6(3H)-one
Sen, A. K.,Mukhopadhyay, Ajoy Kumar
, p. 870 - 873 (2007/10/02)
4-Amino-5-carboxamido-1,3-dimethylimidazolium toluene-p-sulphonate (II) undergoes Dimroth type rearrangement smoothly with basic ion-exchange resin to give 1-methyl-4-methylaminoimidazole-5-carboxamide (III). 4-Amino-5-carboxamido-3-(6-methoxy-8-quinolyl)-1-methylimidazolium toluene-p-sulphonate (VI) and 4-amino-5-cyano-1-methyl-3-(4-sulphamoylphenyl)imidazolium toluene-p-sulphonate (XIII) also undergo similar rearrangement to furnish 4-(6-methoxy-8-quinolylamino)-1-methylimidazole-5-carboxamide (VII) and 5-cyano-1-methyl-4-(4-sulphamoylanilino)imidazole (XIV) respectively.The latter (XIV) on hydrolysis affords 1-methyl-4-(4-sulphamoylanilino)imidazole-5-carboxamide (XV).Formamide cyclization of VII gives 3-(6-methoxy-8-quinolyl)-7-methylpurin-6(3H)-one (VIII).Efforts to produce the related purines from XV have been unsuccessful. 5-Amino-1-(4-sulphamoylphenyl)imidazole-4-carboxamide (X) when treated with DMF-POCl3 complex produces 4-cyano-5-(N,N-dimethylaminomethyleneamino)-1-(4-N,N-dimethylaminomethylenesulphamoylphenyl)imidazole (XI).
