Efficient one-pot synthesis of spiro[indoline-3,4′-pyrazolo[3,4-e][1,4]thiazepine]dione via three-component reaction

被引：58
作者：
Chen, Hui [1 ]
Shi, Daqing [1 ]
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
来源：
TETRAHEDRON | 2011年 / 67卷 / 31期
关键词：
One-pot synthesis; Spirooxindole derivatives; Multi-component reactions; 1,4-Thiazepine derivatives; SOLVENT-FREE SYNTHESIS; MARINE-DERIVED FUNGUS; SOLID-PHASE SYNTHESIS; SPIROOXINDOLE DERIVATIVES; HETEROCYCLIC-COMPOUNDS; FACILE SYNTHESIS; AQUEOUS-MEDIUM; CITRINADIN-A; INHIBITORS; ACID;
D O I：
10.1016/j.tet.2011.05.069
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient one-pot synthesis of spiro[indoline-3,4'-pyrazolo[3,4-e][1,4]thiazepine] dione derivatives via three-component reaction of 5-amino-3-methylpyrazole, isatin, and thioacid is described. This new protocol produces novel heptacyclic spirooxindole derivatives in good yields in comparison to conventional pentacyclic compounds. This method proceeds through a 3-(5-aminopyrazol-3-yl)-3-hydroxy-2-oxindoline intermediate (Baylis-Hillman type adduct), unlike 3-indolylimine (the intermediate like Shiff-Bases) as in conventional methods. The structure of one representative compound has been confirmed by X-ray diffraction analysis. (C) 2011 Published by Elsevier Ltd.
引用
收藏
页码：5686 / 5692
页数：7
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