Synthesis and tautomerism of spiro-pyrazolines

被引：15

作者：

Dadiboyena, Sureshbabu ^{[1
]}

Valente, Edward J. ^{[2
]}

Hamme, Ashton T., II ^{[1
]}

机构：

[1] Jackson State Univ, Dept Chem & Biochem, Jackson, MS 39217 USA

[2] Univ Portland, Dept Chem, Portland, OR 97203 USA

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 14期

基金：

美国国家卫生研究院;

关键词：

Spiro-pyrazolines; 1,3-Dipolar cycloaddition; Tautomerism; Heterocycles; Indolines; Regioselectivity; MARINE SPONGE METABOLITES; 1,3-DIPOLAR CYCLOADDITION; CONSTRUCTION; DERIVATIVES; ISOXAZOLINES; VERONGAMINE; CYCLIZATION; CELECOXIB; ANALOGS; ROUTE;

D O I：

10.1016/j.tetlet.2014.02.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An experimental study on the synthesis, tautomerism, and acid promoted structural changes of spiro-pyrazolines is described. The target was achieved through a [3+2]-dipolar cycloaddition of an alkene with nitrile imines generated in situ and was isolated in high yield. The synthesized cycloadduct displayed a tendency to exhibit an imine-enamine type of tautomerism as evidenced by X-ray crystal and NMR studies. Furthermore, addition of an acid resulted in the transformation of an imine tautomer to an enamine. The current report constitutes a first formal observation of this kind of tautomerism observed in spiro-indoline pyrazolines. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：2208 / 2211

页数：4

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