PURINES, PYRIMIDINES, AND IMIDAZOLES .51. NEW SYNTHESES OF SOME 5-ALKYL-AMINOIMIDAZOLES AND 5-DIALKYL-AMINOIMIDAZOLES - 3-ALKYLIMIDAZOLIUM NUCLEOSIDES AND 3-ALKYLPURINES

被引:15
作者
BROWN, T [1 ]
KADIR, K [1 ]
MACKENZIE, G [1 ]
SHAW, G [1 ]
机构
[1] UNIV BRADFORD,SCH CHEM,BRADFORD BD7 1DP,W YORKSHIRE,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 12期
关键词
D O I
10.1039/p19790003107
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ethyl 3-methyl-5-amino-1-(2,3-O-isopropylidene-a- and -β-D- ribofuranosyl)imidazolium-4-carboxylate iodides, the corresponding benzyl-β-D-ribofuranosyl ester, and benzyl 3-methyl-5-amino-1-(2,3,5-tri-O- acetyl-β-D-ribofuranosyl)imidazolium-4-carboxylate iodide have been prepared by methylation of the corresponding nucleosides with methyl iodide. Their reactions with acids and bases have been examined. Ethyl 4(5)-methylamino- and dimethylamino-imidazole-5(4)-carboxylates have been prepared in a sequence of reactions from ethyl cyanoacetate and the former compound was converted into 3-methylhypoxanthine by heating with formamidine acetate and into 3-methylguanine by a sequence of reactions. The methylamino-derivative undergoes a Dimroth rearrangement when heated with aqueous ammonia, to produce 1-methyl-5-aminoimidazole-carboxamide.
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页码:3107 / 3112
页数:6
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