Substituent effects in the ring-chain tautomerism of 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e] [1,3]oxazines

被引：97

作者：

Szatmári, I ^{[1
]}

Martinek, TA ^{[1
]}

Lázár, L ^{[1
]}

Fülöp, F ^{[1
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary

来源：

TETRAHEDRON | 2003年 / 59卷 / 16期

基金：

匈牙利科学研究基金会;

关键词：

amino alcohols; oxazines; substituent effects; tautomerism;

D O I：

10.1016/S0040-4020(03)00331-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of Betti base analogue amino naphthols with substituted benzaldehydes led to 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines (3-9) which proved to be three-component (r(1)-o-r(2)) tautomeric mixtures in CDCl3 at 300 K. The electronic effects of the 3-aryl groups on the ratios of the ring-chain tautomeric forms at equilibrium could be described by the equation log K-X=rhosigma(+)+log K-X=H. The value of the intercept was found to be strongly influenced by the steric arrangement of the 1,3-diaryl substituents. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：2877 / 2884

页数：8

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