A SIMPLE AND EFFICIENT SYNTHESIS OF 9-SUBSTITUTED GUANINES - CYCLODESULFURIZATION OF 1-SUBSTITUTED 5-[(THIOCARBAMOYL)AMINO]IMIDAZOLE-4-CARBOXAMIDES UNDER AQUEOUS BASIC CONDITIONS

被引：25

作者：

ALHEDE, B ^{[1
]}

CLAUSEN, FP ^{[1
]}

JUHLCHRISTENSEN, J ^{[1
]}

MCCLUSKEY, KK ^{[1
]}

PREIKSCHAT, HF ^{[1
]}

机构：

[1] GEA LTD PHARMACEUT MFG CO,DEPT CHEM,HOLGER DANSKESVEJ 89,DK-2000 COPENHAGEN,DENMARK

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 06期

关键词：

D O I：

10.1021/jo00006a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Aminoimidazole-4-carboxamide (AICA) (1a) is 1-alkylated by an improved method. The resulting 5-amino-1-alkylimidazole-4-carboxamides (1b-i) are converted to the corresponding 1-alkyl-5-[(thiocarbamoyl)-amino]imidazole-4-carboxamides (3). These compounds are ring closed under alkaline conditions to 9-substituted guanines (5) in very high yields by treatment with heavy-metal salts in aqueous sodium hydroxide, or, in somewhat lower yields, by S-oxidation with hydrogen peroxide or sodium perborate in aqueous sodium hydroxide.

引用

页码：2139 / 2143

页数：5

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