Michael Addition of Aryl Thiols to 3-(2,2,2-Trifluoroethylidene)Oxindoles under Catalyst-Free Conditions: The Rapid Synthesis of Sulfur-Containing Oxindole Derivatives

2018 ◽  
Vol 42 (4) ◽  
pp. 210-214
Author(s):  
Bo Chen ◽  
Jiaheng Lei ◽  
Junling Zhao
Keyword(s):  
Michael Addition ◽  
Room Temperature ◽  
Rapid Synthesis ◽  
Efficient Catalyst ◽  
Mild Conditions ◽  
Catalyst Free ◽  
Wide Range ◽  
High Yields ◽  
The Michael Addition ◽  
Sulfur Containing

A mild and efficient catalyst-free method for the rapid synthesis at room temperature of 3-thiomethylated oxindole derivatives has been achieved via the Michael addition of aryl thiols to ring and 1-substituted 3-(2,2,2-trifluoroethylidene)oxindoles in dichloromethane. The method was applicable to a wide range of thiols and variously substituted 3-(2,2,2-trifluoroethylidene)oxindoles under mild conditions as demonstrated by the synthesis in high yields with good diastereoselectivities of 30 3-thiomethylated oxindoles bearing a trifluoromethyl group.

scholarly journals Ammonia borane enabled upgrading of biomass derivatives at room temperature

2020 ◽  
Vol 22 (18) ◽  
pp. 5972-5977
Author(s):  
Wenfeng Zhao ◽  
Sebastian Meier ◽  
Song Yang ◽  
Anders Riisager
Keyword(s):  
Room Temperature ◽  
Value Added ◽  
Ammonia Borane ◽  
Efficient Catalyst ◽  
Free System ◽  
Mild Conditions ◽  
Catalyst Free ◽  
Value Added Products

An efficient catalyst-free system composed of ammonia borane in water or alcohol was developed to selectively convert biomass-derived feedstock into four value-added products under extremely mild conditions.

scholarly journals Cyanuric Chloride as an Efficient Catalyst for the Synthesis of 2,3-UnsaturatedO-Glycosides by Ferrier Rearrangement

2014 ◽  
Vol 2014 ◽  
pp. 1-6
Author(s):  
Xiaojuan Yang ◽  
Na Li
Keyword(s):  
Room Temperature ◽  
Cyanuric Chloride ◽  
Efficient Catalyst ◽  
Experimental Procedure ◽  
Wide Range ◽  
Ferrier Rearrangement ◽  
High Yields

Cyanuric chloride has been found to be an efficient catalyst for the synthesis of 2,3-unsaturatedO-glycosides from the reaction of 3,4,6-tri-O-acetyl-D-glucal and a wide range of alcohols in dichloromethane at room temperature. The experimental procedure is simple, and the products are obtained in high yields.

scholarly journals Chemoselective aza-Michael addition of indoles to 2-aroyl-1,3-diarylenones

2019 ◽  
Vol 44 (1-2) ◽  
pp. 97-103
Author(s):  
Zheng Li ◽  
Aizhen Yang ◽  
Xiaolong Ma ◽  
Zhenrong Liu
Keyword(s):  
Transition Metal ◽  
Michael Addition ◽  
Potassium Hydroxide ◽  
Room Temperature ◽  
Transition Metal Catalysts ◽  
Atom Economy ◽  
Mild Conditions ◽  
High Yields ◽  
Work Up ◽  
Aryl Methyl

A total of 20 examples of 2-[(1 H-indol-1-yl)(aryl)methyl]-1,3-diphenylpropane-1,3-diones were efficiently synthesized by the aza-Michael addition at the N1 position of indoles with 2-aroyl-1,3-diarylenones at room temperature in the presence of potassium hydroxide. The salient features of this protocol are no transition-metal catalysts, mild conditions, high chemoselectivity, high atom economy, high yields, and a simple work-up procedure.

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.

scholarly journals A New Heterogeneous Catalyst Obtained via Supramolecular Decoration of Graphene with a Pd2+ Azamacrocyclic Complex

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2714 ◽  
Author(s):  
Matteo Savastano ◽  
Paloma Arranz-Mascarós ◽  
Maria Paz Clares ◽  
Rafael Cuesta ◽  
Maria Luz Godino-Salido ◽  
...  
Keyword(s):  
Heterogeneous Catalyst ◽  
Self Assembly ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Assembly Process ◽  
Efficient Catalyst ◽  
Mild Conditions ◽  
Cross Coupling Reaction ◽  
Green Procedure

A new G-(H2L)-Pd heterogeneous catalyst has been prepared via a self-assembly process consisting in the spontaneous adsorption, in water at room temperature, of a macrocyclic H2L ligand on graphene (G) (G + H2L = G-(H2L)), followed by decoration of the macrocycle with Pd2+ ions (G-(H2L) + Pd2+ = G-(H2L)-Pd) under the same mild conditions. This supramolecular approach is a sustainable (green) procedure that preserves the special characteristics of graphene and furnishes an efficient catalyst for the Cu-free Sonogashira cross coupling reaction between iodobenzene and phenylacetylene. Indeed, G-(H2L)-Pd shows an excellent conversion (90%) of reactants into diphenylacetylene under mild conditions (50 °C, water, aerobic atmosphere, 14 h). The catalyst proved to be reusable for at least four cycles, although decreasing yields down to 50% were observed.

Uncatalyzed, on water oxygenative cleavage of inert C–N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives

2019 ◽  
Vol 21 (7) ◽  
pp. 1735-1742 ◽  
Author(s):  
Vinayak Botla ◽  
NavyaSree Pilli ◽  
Chandrasekharam Malapaka
Keyword(s):  
Room Temperature ◽  
Efficient Catalyst ◽  
Catalyst Free ◽  
One Step

Oxygenative cleavage of an inert CAr–NH2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is achieved through an efficient, catalyst free, one step synthesis of 8-benzyloxy, 7-aminoquinoline directly from 8-aminoquinoline in water at room temperature.

p-Toluenesulfonic Acid Coated Natural Phosphate as an Efficient Catalyst for the Synthesis of 2-Substituted Benzimidazole

2018 ◽  
Vol 42 (12) ◽  
pp. 614-617
Author(s):  
Soumia Belkharchach ◽  
Hanane Elayadi ◽  
Hana Ighachane ◽  
Said Sebti ◽  
Mustapha Ait Ali ◽  
...  
Keyword(s):  
Environmentally Friendly ◽  
Catalytic Amount ◽  
Reusable Catalyst ◽  
Efficient Catalyst ◽  
Natural Phosphate ◽  
Mild Conditions ◽  
Toluenesulfonic Acid ◽  
High Yields

2-Substituted benzimidazoles are selectively synthesised in high yields via the condensation of o-phenylenediamine derivatives with aldehyde derivatives using catalytic amount of p-toluenesulfonic acid coated natural phosphate (NP/PTSA) under mild conditions. The use of NP/PTSA as a reusable catalyst makes this process simple, convenient, and environmentally friendly.

SiO2·12WO3·24H2O: a Highly Efficient Catalyst for the Synthesis of 5-Arylidene Barbituric Acid in the Presence of Water

2009 ◽  
Vol 62 (4) ◽  
pp. 353 ◽  
Author(s):  
Ji-Tai Li ◽  
Ming-Xuan Sun
Keyword(s):  
Room Temperature ◽  
Barbituric Acid ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Efficient Route ◽  
Acid Catalyzed ◽  
High Yields

The condensation of aromatic aldehydes and barbituric acid catalyzed by SiO2·12WO3·24H2O in aqueous media at room temperature gave 5-arylidene barbituric acid in high yields with or without the use of ultrasound, providing a simple and efficient route to synthesis of these compounds.

Direct catalytic synthesis of densely substituted 3-formylpyrroles from imines and 1,4-ketoaldehydes

RSC Advances ◽  
2014 ◽  
Vol 4 (65) ◽  
pp. 34548-34551 ◽  
Author(s):  
Indresh Kumar ◽  
Nisar A. Mir ◽  
Panduga Ramaraju ◽  
Deepika Singh ◽  
Vivek K. Gupta ◽  
...  
Keyword(s):  
Room Temperature ◽  
Catalytic Synthesis ◽  
Mild Conditions ◽  
High Yields

An organocatalytic formal [3 + 2] cycloaddition have been developed between 1,4-ketoaldehydes and imines to synthesize densely substituted 3-formylpyrroles in high yields (up to 70%) under mild conditions at room temperature.

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