Theoretical estimation of the annular tautomerism of indazoles

被引：54

作者：

Alkorta, I ^{[1
]}

Elguero, J ^{[1
]}

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2005年 / 18卷 / 08期

关键词：

indazole; tautometism; AMI; B3LYP; Free-Wilson models;

D O I：

10.1002/poc.923

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Theoretical calculations at semi-empirical AMI and density functional B3LYP/6-31G* levels were carried out on 52 NH-indazoles. Although in most cases the 1H-tautomer is the most stable, we found several indazoles for which the 2H-tautomer is more stable than the 1H-tautomer. The differences in energy between the 1H-and 2H-tautomers were interpreted in terms of substituent effects with the use of a Free-Wilson (presence-absence) matrix. Copyright (c) 2005 John Wiley & Sons, Ltd.

引用

页码：719 / 724

页数：6

共 36 条

[1] Tautomerism and the Mills-Nixon-like effect in pyrazoles [J].

Alkorta, I ;

Elguero, J .

STRUCTURAL CHEMISTRY, 1997, 8 (03) :189-195

[2]

ALKORTA I, 1991, J MOL STRUCT, V228, P47

[3]

Bader R. F. W., 1990, ATOMS MOL QUANTUM TH, V22

[4] THE STRUCTURE OF INDAZOLINONE AND DERIVATIVES IN THE SOLID-STATE AND IN SOLUTION - AN X-RAY AND NUCLEAR-MAGNETIC-RESONANCE STUDY [J].

BALLESTEROS, P ;

ELGUERO, J ;

CLARAMUNT, RM ;

FAURE, R ;

FOCESFOCES, MD ;

CANO, FH ;

ROUSSEAU, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (11) :1677-1681

[5] Progress towards the discovery of xanthine oxidase inhibitors [J].

Borges, F ;

Fernandes, E ;

Roleira, F .

CURRENT MEDICINAL CHEMISTRY, 2002, 9 (02) :195-217

[6] C-13 NMR CHEMICAL-SHIFTS OF N-UNSUBSTITUTED-METHYL-PYRAZOLE AND N-METHYL-PYRAZOLE DERIVATIVES [J].

CABILDO, P ;

CLARAMUNT, RM ;

ELGUERO, J .

ORGANIC MAGNETIC RESONANCE, 1984, 22 (09) :603-607

[7] BASICITY AND ACIDITY OF AZOLES - THE ANNELATION EFFECT IN AZOLES [J].

CATALAN, J ;

CLARAMUNT, RM ;

ELGUERO, J ;

LAYNEZ, J ;

MENENDEZ, M ;

ANVIA, F ;

QUIAN, JH ;

TAAGEPERA, M ;

TAFT, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4105-4111

[8] Importance of aromaticity on the relative stabilities of indazole annular tautomers: An ab initio study [J].

Catalan, J ;

dePaz, JLG ;

Elguero, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (01) :57-60

[9] DESCRIPTION OF HETEROCYCLIC SUBSTITUENTS - A FREE-WILSON TYPE APPROACH USING D-OPTIMAL DESIGNS [J].

CATIVIELA, C ;

GARCIA, JI ;

ELGUERO, J ;

MATHIEU, D ;

LUU, RPT .

QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS, 1987, 6 (04) :173-178

[10]

CATIVIELA C, 1983, EUR J MED CHEM, V18, P359

← 1 2 3 4 →