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.
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收藏
页码：2208 / 2211
页数：4
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