Catalytic application of task specific ionic liquid on the synthesis of benzoquinazolinone derivatives by a multicomponent reaction

被引：37

作者：

Rahman, Matiur ^{[1
]}

Sarkar, Anirban ^{[1
]}

Ghosh, Monoranjan ^{[1
]}

Majee, Adinath ^{[1
]}

Hajra, Alakananda ^{[1
]}

机构：

[1] Visva Bharati Cent Univ, Dept Chem, Santini Ketan 731235, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 01期

关键词：

Ionic liquid; Benzoquinazolin-2-one; Biginelli reaction; Hydrogen bond; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; CYCLOCONDENSATION REACTION; 1,3-DICARBONYL COMPOUNDS; BIGINELLI REACTION; GREEN CHEMISTRY; SILICA-GEL; SOLVENT; DIHYDROPYRIMIDINONES; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES;

D O I：

10.1016/j.tetlet.2013.11.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzoquinazolin-2-one derivatives were synthesized by using a catalytic amount of task specific ionic liquid, [1-methyl-3-(4-sulfobutyl)imidazolium-4-methylbenzenesulfonate] through a one-pot multicomponent Biginelli reaction of a-tetralone, aldehyde, and urea/thiourea in excellent yields within a short reaction time. Mechanism studies suggest that the reaction proceeds through iminium intermediate and C2-H of the TSIL plays a major role on its catalytic activity. The catalyst has been reused four times without any significant loss in catalytic activity. Large scale reaction by using this TSIL suggests the applicability of this methodology for bulk synthesis of quinazolinone derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：235 / 239

页数：5

共 54 条

[1] Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses
Abelman, MM
Smith, SC
James, DR
[J]. TETRAHEDRON LETTERS, 2003, 44 (24) : 4559 - 4562
[2] The role of catalysis in the design, development, and implementation of green chemistry
Anastas, PT
Bartlett, LB
Kirchhoff, MM
Williamson, TC
[J]. CATALYSIS TODAY, 2000, 55 (1-2) : 11 - 22
[3] Amphiphilic Organocatalyst for Schotten-Baumann-Type Tosylation of Alcohols under Organic Solvent Free Condition
Asano, Keisuke
Matsubara, Seijiro
[J]. ORGANIC LETTERS, 2009, 11 (08) : 1757 - 1759
[4] KA1(SO4)2•12H2O supported on silica gel as a novel heterogeneous system catalyzed biginelli reaction -: One-pot synthesis of di-hydropyrimidinones under solvent-free conditions
Azizian, J
Mohammadi, AA
Karimi, AR
Mohammadizadeh, MR
[J]. APPLIED CATALYSIS A-GENERAL, 2006, 300 (01) : 85 - 88
[5] Biginelli P., 1891, Berichte Der Deutschen Chemischen Gesellschaft, V24, P2962, DOI 10.1002/cber.189102402126
[6] Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[7] Catalytic application of room temperature ionic liquids:: [bmim][MeSO4] as a recyclable catalyst for synthesis of bis(indolyl) methanes. Ion-fishing by MALDI-TOF-TOF MS and MS/MS studies to probe the proposed mechanistic model of catalysis
Chakraborti, Asit K.
Roy, Sudipta Raha
Kumar, Dinesh
Chopra, Pradeep
[J]. GREEN CHEMISTRY, 2008, 10 (10) : 1111 - 1118
[8] On Catalysis by Ionic Liquids
Chakraborti, Asit K.
Roy, Sudipta Raha
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) : 6902 - +
[9] Catalysis for green chemistry
Clark, JH
[J]. PURE AND APPLIED CHEMISTRY, 2001, 73 (01) : 103 - 111
[10] Green Chemistry: challenges and opportunities
Clark, JH
[J]. GREEN CHEMISTRY, 1999, 1 (01) : 1 - 8

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