An expedient four-component domino protocol for the regioselective synthesis of highly functionalized pyranopyrazoles and chromenopyrazoles via nitroketene-N,S-acetal chemistry under solvent-free condition

被引：28
作者：
Jayabal, Kamalraja [1 ]
Paramasivan, Thirumalai Perumal [1 ]
机构：
[1] CSIR, Cent Leather Res Inst, Div Organ Chem, Chennai 600020, Tamil Nadu, India
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 12期
关键词：
Domino reaction; Greener approach; Regioselective synthesis; Nitroketene-N; S-acetal chemistry; Pyranopyrazoles and chromenopyrazoles; ONE-POT; ORGANIC-SYNTHESIS; ANTIMICROBIAL EVALUATION; MULTICOMPONENT SYNTHESIS; HETEROCYCLIC-COMPOUNDS; MOLLUSCICIDAL ACTIVITY; ATOM ECONOMY; DERIVATIVES; EFFICIENT; GREEN;
D O I：
10.1016/j.tetlet.2014.02.019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Combinatorial library of pyranopyrazoles and chromenopyrazoles was regioselectively synthesized in excellent yield from ethylacetoacetate, hydrazinehydrate, substituted aldehyde/salicylaldehyde with nitroketene-N,S-acetal in the presence of piperidine under solvent-free condition (SFC) in an eco-benign manner. This novel strategy excludes tedious extraction, chromatographic separation and recrystallization processes. The final product could be obtained by simple filtration by the addition of ethanol to the reaction mixture. This domino protocol generates biologically significant heterocycles with the formation of C-C, C=C, C-N, C=N, C-O bonds and one stereo-centre in a single operation via condensation/Knoevenagel/Michael/annulation sequences. (c) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2010 / 2014
页数：5
相关论文
共 102 条
[1]   Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives [J].
Abdelrazek, Fathy M. ;
Metz, Peter ;
Kataeva, Olga ;
Jaeger, Anne ;
El-Mahrouky, Sherif F. .
ARCHIV DER PHARMAZIE, 2007, 340 (10) :543-548
[2]   Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives [J].
Abdelrazek, Fathy M. ;
Metz, Peter ;
Metwally, Nadia H. ;
El-Mahrouky, Sherif F. .
ARCHIV DER PHARMAZIE, 2006, 339 (08) :456-460
[3]  
Abu T. B., 2012, J MED CHEM, V55, P961
[4]  
Ahluwalia VK, 1997, INDIAN J CHEM B, V36, P88
[5]  
Andreani L.L., 1960, BOLL CHIM FARM, V99, P583
[6]  
[Anonymous], 1983, COLUMBIA LAW REV, V83
[7]  
[Anonymous], HARVARD DESIGN M SPR
[8]  
[Anonymous], [No title captured], Patent No. 2004009589
[9]   Michael addition of α-azido ketones on iminocoumarin derivatives: an efficient access to new functionalized azido chromenes [J].
Babu, Thelagathoti Hari ;
Kamalraja, Jayabal ;
Muralidharan, Doraiswamy ;
Perumal, Paramasivan T. .
TETRAHEDRON LETTERS, 2011, 52 (32) :4093-4096
[10]   An eco-friendly sequential catalyst- and solvent-free four-component stereoselective synthesis of novel 1,4-pyranonaphthoquinones [J].
Bala, Balasubramanian Devi ;
Rajesh, Stephen Michael ;
Perumal, Subbu .
GREEN CHEMISTRY, 2012, 14 (09) :2484-2490
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