1,8-Diazabicyclo[5.4.0]-undec-7-ene based protic ionic liquids and their binary systems with molecular solvents catalyzed Michael addition reaction

2020 ◽  
Vol 44 (32) ◽  
pp. 13701-13706
Author(s):  
Gulshan Ara ◽  
Muhammed Shah Miran ◽  
Md. Mominul Islam ◽  
M. Yousuf A. Mollah ◽  
M. Muhibur Rahman ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Ionic Liquids ◽  
Michael Addition ◽  
Binary Systems ◽  
Addition Reaction ◽  
Michael Addition Reaction ◽  
Protic Ionic Liquids ◽  
Molecular Solvents

Michael addition reaction of acetylacetone and cyclohexenone has been studied using 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) based protic ionic liquids and their binary systems with DBU, water and acetic acid as catalysts.

scholarly journals Thin Layer Chromatography-A Tool to Investigate Kinetics of Michael Addition Reaction

2018 ◽  
Vol 10 (3) ◽  
pp. 323-329 ◽  
Author(s):  
M. A. B. H. Susan ◽  
G. Ara ◽  
M. M. Islam ◽  
M. M. Rahman ◽  
M. Y. A. Mollah
Keyword(s):  
Ionic Liquids ◽  
Thin Layer ◽  
Thin Layer Chromatography ◽  
Michael Addition ◽  
Binary Systems ◽  
Addition Reaction ◽  
Average Rate ◽  
Michael Addition Reaction ◽  
Layer Chromatography ◽  
Kinetics Of

Thin layer chromatography (TLC), a tool for defining identity, purity, and quantitation of a compound, has also been proved useful for monitoring the progress of a chemical reaction. However, the   technique is yet to be exploited for investigating the kinetics of a reaction systematically. In this work, we used TLC for measuring the time for consumption of a reactant in Michael addition reaction of acetylacetone with 2-cyclohexene-1-one. Average rate of the model reaction was determined using a definite initial concentration of acetylacetone for a series of catalyst systems like NaOH, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), DBU based protic ionic liquids (PILs) 1,8-diazabicyclo[5.4.0]undec-7-ene-8-ium hydroxide ([HDBU]OH) and 1,8-diazabicyclo[5.4.0]undec-7-ene-8-ium acetate ([HDBU]CH3COO), a DBU based aprotic ionic liquid (AIL), 8-hexyl-1,8-diazabicyclo [5.4.0]undec-7-ene-8-ium hydroxide ([C6DBU]OH), and binary systems of the ionic liquids with molecular solvents, such as, water, DBU, and acetic acid. The kinetic data on the performance of the chosen catalysts were interpreted on the basis of the established mechanism of the reaction. Finally, the prospect of the method based on TLC as a suitable technique for kinetic study of chemical reactions has been discussed.

Effect of Superbasic Ionic Liquids on the Synthesis of Dendritic PolyaminesviaAza-Michael Addition Reaction

2017 ◽  
Vol 2 (31) ◽  
pp. 10020-10026
Author(s):  
Bartłomiej Bereska ◽  
Krystyna Czaja ◽  
Janusz Nowicki ◽  
Jolanta Iłowska ◽  
Agnieszka Bereska ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction

Novel Brønsted Acidic Ionic Liquids Based on Benzimidazolium Cation: Synthesis and Catalyzed Conjugate Addition of Indoles with α,β-unsaturated Ketones

2011 ◽  
Vol 233-235 ◽  
pp. 977-984
Author(s):  
Bin Wang ◽  
Chen Jiang Liu
Keyword(s):  
Ionic Liquids ◽  
Michael Addition ◽  
Addition Reaction ◽  
Conjugate Addition ◽  
Michael Addition Reaction ◽  
Unsaturated Ketones ◽  
Mild Conditions ◽  
Acidic Ionic Liquids ◽  
High Yields ◽  
The Michael Addition

Brønsted acidic ionic liquids based on benzimidazolium cation was synthesized and employed as an efficient catalysts for the Michael addition reaction of indoles to α,β-unsaturated ketones under mild conditions to afford the corresponding conjugate addition products in high yields (90%-98%). The catalyst 1-butyl-3-(3-sulfopropyl)benzimidazolium p-toluenesulfonate ([PSbbim][p-CH3PhSO3]) could be reused at least three times without a noticeably decrease in its activity.

Natural Sugars Derived Chiral Ionic Liquids for Asymmetric Michael Addition Reaction

2016 ◽  
Vol 1 (10) ◽  
pp. 2341-2343 ◽  
Author(s):  
R. Jayachandra ◽  
Sabbasani Rajasekhara Reddy ◽  
Balakrishna
Keyword(s):  
Ionic Liquids ◽  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction ◽  
Chiral Ionic Liquids ◽  
Asymmetric Michael Addition

Cupin Variants as Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes

2019 ◽  
Author(s):  
Nobutaka Fujieda ◽  
Miho Yuasa ◽  
Yosuke Nishikawa ◽  
Genji Kurisu ◽  
Shinobu Itoh ◽  
...  
Keyword(s):  
Michael Addition ◽  
In Silico ◽  
Addition Reaction ◽  
Single Point ◽  
Point Mutations ◽  
Unsaturated Ketone ◽  
Michael Addition Reaction ◽  
Beta Barrel ◽  
Cupin Superfamily ◽  
Single Point Mutations

Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double-stranded beta-barrel structure ligating to a Cu ion through histidine side chains. Variegating the first coordination sphere of TM1459 revealed that H52A and H54A/H58A mutants effectively catalyzed the diastereo- and enantio-selective Michael addition reaction of nitroalkanes to an α,β-unsaturated ketone. Moreover, in silico substrate docking signified C106N and F104W single-point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

Synthesis ◽  
2021 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Petr Beier ◽  
Maryam Khalili Foumeshi ◽  
Ali Alaei ◽  
Blanka Klepetářová
Keyword(s):  
Amino Acids ◽  
Carbon Disulfide ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Addition Reaction ◽  
Primary Amines ◽  
Oxidation Reactions ◽  
Michael Addition Reaction ◽  
Synthetic Utility ◽  
Reaction Proceeds

AbstractThiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. By using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.

Bisphosphine catalyzed sequential [3 + 2] cycloaddition and Michael addition of ynones with benzylidenepyrazolones via dual α′,α′-C(sp3)–H bifunctionalization to construct cyclopentanone-fused spiro-pyrazolones

2018 ◽  
Vol 16 (48) ◽  
pp. 9461-9471 ◽  
Author(s):  
Jiayong Zhang ◽  
Zhiwei Miao
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction

A sequential [3 + 2] cycloaddition and Michael addition reaction of ynones with benzylidenepyrazolones afforded cyclopentanone-fused spiro-pyrazolones catalyzed by DPPB via dual α′,α′-C(sp3)–H bifunctionalization.

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