New multicomponent domino reaction on water: highly diastereoselective synthesis of spiro[indoline-3,4′-pyrazolo[3,4-b]pyridines] catalyzed by NaCl

被引：62
|
作者：
Dandia, Anshu [1 ]
Laxkar, Ashok Kumar [1 ]
Singh, Ruby [1 ]
机构：
[1] Univ Rajasthan, Dept Chem, Ctr Adv Studies, Jaipur 302004, Rajasthan, India
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 24期
关键词：
Multicomponent domino reaction; Diastereoselective; Sodium chloride catalyst; Spirooxindole; Pyrazolo-pyridine; Water; SPIROOXINDOLE DERIVATIVES; REGIOSELECTIVE SYNTHESIS; 3-COMPONENT REACTION; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; HETEROCYCLES; TRACAZOLATE; RECEPTORS; TANDEM;
D O I：
10.1016/j.tetlet.2012.03.136
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct and efficient approach for the preparation of medicinally promising pyrazolopyridinyl spirooxindoles has been developed through a sequential one-pot, three-component reaction of easily available isatin, alpha-cyanoacetic ester or malononitrile, and 5-amino-3-methylpyrazole catalyzed by sodium chloride in water. Desired products were obtained in high to excellent yields using a simple workup procedure. The product synthesized using alpha-cyanoacetic ester showed high diastereoselectivity in which the stereochemistry of major diastereomer was confirmed by X-ray diffraction analysis. The present green synthesis shows attractive characteristics such as the use of water as the reaction medium, one pot conditions, short reaction period, easy workup/purification, and reduced waste production, without use of any acid or metal promoters. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3012 / 3017
页数：6
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