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

页码：3201 / 3208

页数：8

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