New four-component reactions in water: a convergent approach to the metal-free synthesis of spiro[indoline/acenaphthylene-3,4′-pyrazolo[3,4-b]pyridine derivatives

被引：57
|
作者：
Balarnurugan, Kamaraj [1 ]
Perumal, Subbu [1 ]
Menendez, J. Carlos [2 ]
机构：
[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India
[2] Univ Complutense, Dept Quim Organ & Farmaceut, Fac Farm, E-28040 Madrid, Spain
来源：
TETRAHEDRON | 2011年 / 67卷 / 18期
关键词：
Multi-component reactions; Domino reactions; Water as reaction medium; Spirooxindoles; Fused pyrazoles; SPIRO-PYRIDO-PYRROLIZINES; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; REGIOSELECTIVE-SYNTHESIS; ORGANIC-REACTIONS; 3-COMPONENT SYNTHESIS; TANDEM PROTOCOL; AQUEOUS-MEDIA; CHEMISTRY; SOLVENT;
D O I：
10.1016/j.tet.2011.03.020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New four-component domino reactions are described that allow the one-pot synthesis of spiro[indoline/acenaphthylene-3,4'-pyrazolo[3,4-b]pyridine derivatives from the reaction of phenylhydrazine, 3-aminocrotononitrile, isatin/acenaphthylene-1,2-dione, and cyclic 1,3-dicarbonyl compounds, including cyclohexane-1,3-diones, barbituric acid, and 2-thioxodihydropyrimidine-4,6(1H,5H)-dione, in the presence of (+/-)-camphor-10-sulfonic acid (CSA). These processes take place in water and involve the generation of two rings and five new bonds (two C-C, two C-N and one C = N) in a single synthetic operation, with expedient work-up and diminished waste generation due to the absence of extraction and purification steps. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3201 / 3208
页数：8
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