A facile synthesis of pyrazoles with multi-point structural diversity by 1,3-dipolar cycloaddition

被引：22
作者：
Cheung, Kwai Ming J. [1 ]
Reynisson, Johannes [1 ]
McDonald, Edward [1 ]
机构：
[1] Inst Canc Res, Canc Res UK Canc Therapeut Unit, Sutton SM2 5NG, Surrey, England
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 45期
关键词：
Pyrazole; 1,3-Dipolar cycloaddition; HOMO-LUMO; ANTI-DIABETIC ACTIVITY; IN-VITRO; DERIVATIVES; ANTITUMOR; ALKYNES; DESIGN; POTENT;
D O I：
10.1016/j.tetlet.2010.09.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe the synthesis of diverse pyrazoles by 1,3-dipolar cycloaddition of ethyl diazoacetate with various acetylenes in refluxing toluene. The product pyrazoles are useful starting points for preparing a diverse collection of trisubstituted pyrazole carboxamides. For aryl and heteroaryl alkynes a single product is obtained while alkyl alkynes afford a ca. 6:1 mixture of regioisomers. The observed regioselectivity for the cycloaddition step and the ease of reaction are consistent with predictions derived from computing the HOMO-LUMO energies of the reactants. (C) 2010 Published by Elsevier Ltd.
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页码：5915 / 5918
页数：4
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