A novel synthesis of 1,3,5-trisubstituted pyrazoles through a spiro-pyrazoline intermediate via a tandem 1,3-dipolar cycloaddition/elimination

被引：49
作者：
Dadiboyena, Sureshbabu [1 ]
Valente, Edward J. [2 ]
Hamme, Ashton T., II [1 ]
机构：
[1] Jackson State Univ, Dept Chem, Coll Sci Engn & Technol, Jackson, MS 39217 USA
[2] Mississippi Coll, Dept Chem & Biochem, Clinton, MS 39058 USA
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 03期
关键词：
Cycloaddition; Ring fragmentation; Heterocycles; Spirocycles; Tandem reactions; Regioselectivity; NITRILE IMINES; NITROOLEFINS; ISOXAZOLES; HYDRAZONES; CELECOXIB;
D O I：
10.1016/j.tetlet.2008.10.145
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The syntheses of an important class of hitherto unreported 1,3,5-pyrazoles, inspired by all unanticipated eliminatory ring opening are described, The reported pyrazole compounds were constructed through the Huisgen cyclization of 2-methylene-1,3,3-trimethylindoline and an in situ generated nitrile imine. The newly formed spiro-pyrazoline intermediate presumably then undergoes a ring opening/elimination process to afford a pyrazole, as evidenced by single X-ray crystal data. The Current report constitutes the first formal observation of this kind of ring opening involving a spiro-pyrazoline intermediate. Published by Elsevier Ltd.
引用
收藏
页码：291 / 294
页数：4
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