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[BBSA-DBN][HSO4]: a novel –SO3H functionalized Bronsted acidic ionic liquid for easy access of quinoxalines.

Authors :
Patil, Megha U.
Shinde, Sachinkumar K.
Patil, Sandip P.
Patil, Suresh S.
Source :
Research on Chemical Intermediates; Nov2020, Vol. 46 Issue 11, p4923-4938, 16p
Publication Year :
2020

Abstract

A novel –SO<subscript>3</subscript>H difunctionalized Bronsted acidic ionic liquid (BAIL) 1, 5-bis (butanesulphonic acid)-diazobicyclo [4,3,0] non-5-enium hydrogen sulphate [BBSA-DBN][HSO<subscript>4</subscript>] is introduced for efficient synthesis of quinoxalines via condensation of substituted 1,2-diketones and various aromatic 1,2-diamines. It could serve as a dual functional catalyst for these reactions. This method has the advantages of mild reaction conditions, high yields, short reaction times, easy work-up, non-chromatographic separations and being environmentally friendly. This protocol provides an effective and environmentally friendly alternative methodology for production of quinoxalines and extends the chemical utilization of benzil in organic synthesis. This room-temperature-derived ionic liquid is highly acidic due to presence of two –SO<subscript>3</subscript>H groups and two HSO<subscript>4</subscript><superscript>−</superscript> anions. Moreover, the IL [BBSA-DBN][HSO<subscript>4</subscript>] could be easily recovered and reused at least five times without change in its catalytic activity. The formation of IL [BBSA-DBN][HSO<subscript>4</subscript>] was confirmed by <superscript>1</superscript>H, <superscript>13</superscript>C NMR spectroscopic techniques. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
09226168
Volume :
46
Issue :
11
Database :
Complementary Index
Journal :
Research on Chemical Intermediates
Publication Type :
Academic Journal
Accession number :
146320676
Full Text :
https://doi.org/10.1007/s11164-020-04227-3