SUBSTITUENT AND SOLVENT EFFECTS ON THE TAUTOMERIC EQUILIBRIA OF N-SUBSTITUTED ALPHA-(AMINOMETHYLENE)PURINE-6-ACETONITRILE DERIVATIVES

被引：3

作者：

HAMAMICHI, N ^{[1
]}

MIYASAKA, T ^{[1
]}

机构：

[1] SHOWA UNIV, SCH PHARMACEUT SCI, SHINAGAWA KU, TOKYO 142, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1990年 / 38卷 / 12期

关键词：

TAUTOMERIC EQUILIBRIUM; SUBSTITUENT EFFECT; SOLVENT EFFECT; HYDROGEN BONDING; ALPHA-(AMINOMETHYLENE)PURINE-6-ACETONITRILE;

D O I：

10.1248/cpb.38.3253

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Substituent and solvent effects on the tautomeric equilibration (E/Z) of alpha-(N-alkyl and -arylaminomethylene)-9-(methoxymethyl)-9H-purine-6-acetonitriles (3a-q) have been studied by means of proton nuclear magnetic resonance spectroscopy in protic and aprotic solvents at 25-degrees-C. In chloroform-d these compounds (3a-q) exist mainly as the E-form. On the other hand, in methanol-d4 or dimethylsulfoxide-d6 the alkylamines (3a-c), phenylamine (3e), meta- or para-substituted phenylamines (3f-j) and 2,6-disubstituted phenylamines (3p and q) exist mainly as the Z-form, while the trityl compound (3d), and ortho-substituted compounds (3k-o) showed a predominance of the E-form.

引用

页码：3253 / 3256

页数：4

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