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

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 α-tetralone, aldehyde, and urea/thiourea in excellent yields within a s...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 1; pp. 235 - 239
Main Authors Rahman, Matiur, Sarkar, Anirban, Ghosh, Monoranjan, Majee, Adinath, Hajra, Alakananda
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.2014
Elsevier
Subjects
Benzoquinazolin-2-one
Biginelli reaction
Chemistry
Chemistry, Organic
Hydrogen bond
Ionic liquid
Physical Sciences
Science & Technology
Benzoquinazolin-2-one
Biginelli reaction
Ionic liquid
Hydrogen bond
SILICA-GEL
ONE-POT SYNTHESIS
1,3-DICARBONYL COMPOUNDS
EFFICIENT SYNTHESIS
3,4-DIHYDROPYRIMIDIN-2(1H)-ONES
SOLVENT
DIHYDROPYRIMIDINONES
CYCLOCONDENSATION REACTION
GREEN CHEMISTRY
Online AccessGet full text

Cover

More Information
Summary: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 α-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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.11.011