A novel catalyst for the Knoevenagel condensation of aldehydes with malononitrile and ethyl cyanoacetate under solvent free conditions

2006 ◽  
Vol 7 (12) ◽  
pp. 931-935 ◽  
Author(s):  
Manoj B. Gawande ◽  
Radha V. Jayaram
Keyword(s):  
Knoevenagel Condensation ◽  
Ethyl Cyanoacetate ◽  
Solvent Free ◽  
Solvent Free Conditions ◽  
Novel Catalyst

A Facile, Efficient and Solvent-Free Titanium (IV) Ethoxide Catalysed Knoevenagel Condensation of Aldehydes and Active Methylenes

2020 ◽  
Vol 17 (2) ◽  
pp. 107-115
Author(s):  
Manjunatha M. Ramaiah ◽  
Nanjunda Swamy Shivananju ◽  
Priya Babu Shubha
Keyword(s):  
Microwave Irradiation ◽  
Knoevenagel Condensation ◽  
Ethyl Cyanoacetate ◽  
Diethyl Malonate ◽  
Aromatic Aldehydes ◽  
Reaction Rates ◽  
Solvent Free ◽  
Solvent Free Conditions ◽  
Wide Range ◽  
Titanium Ethoxide

: Titanium ethoxide has been employed as a novel and efficient reagent for the Knoevenagel condensation of aldehydes with active methylenes such as diethyl malonate and ethyl cyanoacetate under solvent free conditions to afford substituted olefins in high to excellent yields. The reaction is suitable for a variety of aromatic, aliphatic and heteroaromatic aldehydes with various active methylenes. Parallel to this, microwave irradiation has been utilized to achieve improved reaction rates and enhanced yields. Herein, we illustrated a convenient method for the preparation of α,β-unsaturated compounds using both conventional and microwave irradiation methods. An efficient and solvent free Knoevenagel condensation between aldehydes and active methylenes was developed using titanium ethoxide. The procedure proved to be successful with a wide range of substrates such as aromatic, aliphatic and heterocyclic aldehydes and various active methylenes to afford substituted olefins. The reaction was also carried out under microwave irradiation to accomplish the corresponding olefins with improved reaction rates, yields and cleaner reaction profiles.We have developed an efficient and novel methodology for the synthesis of olefinic compounds by Knoevenagel condensation under solvent-free conditions using titanium ethoxide, for the first time, as a reagent as well as a solvent. This method is appropriate for the synthesis of a variety of aromatic aldehydes containing various electron-donating and withdrawing groups, aliphatic and heteroaromatic aldehydes. The significant advantages offered by this methodology could be applied to various active methylenes in order to offer the corresponding Knoevenagel products. Thus, we believe that this method delivers high conversions, cleaner reaction profiles under solvent-free reaction conditions and shorter reaction times, all of which make it a very useful and attractive approach for the preparation of a wide range of substituted olefins.

ChemInform Abstract: Solvent-Free Microwave Enhanced Knoevenagel Condensation of Ethyl Cyanoacetate with Aldehydes.

ChemInform ◽  
2010 ◽  
Vol 30 (40) ◽  
pp. no-no
Author(s):  
Alok Kumar Mitra ◽  
Aparna De ◽  
Nilay Karchaudhuri
Keyword(s):  
Knoevenagel Condensation ◽  
Ethyl Cyanoacetate ◽  
Solvent Free

Two new calix[4]resorcinarene-based coordination cages adjusted by metal ions for the Knoevenagel condensation reaction

2021 ◽  
Author(s):  
Wen-Yuan Pei ◽  
Bing-Bing Lu ◽  
Jin Yang ◽  
Tianqi Wang ◽  
Jian-Fang Ma
Keyword(s):  
Metal Ions ◽  
Knoevenagel Condensation ◽  
Condensation Reaction ◽  
Solvent Free ◽  
Catalytic Activities ◽  
Solvent Free Conditions ◽  
Coordination Cages ◽  
Knoevenagel Condensation Reaction

Two new calix[4]resorcinarene-based metal-coordinated cages have been synthesized through tuning metal ions, where they featured catalytic activities for the Knoevenagel condensation reaction under solvent-free conditions.

A solvent-free protocol for the green synthesis of arylalkylidene rhodanines in a task-specific ionic liquid

2010 ◽  
Vol 88 (6) ◽  
pp. 514-518 ◽  
Author(s):  
Abdolhamid Alizadeh ◽  
Mohammad M. Khodaei ◽  
Ali Eshghi
Keyword(s):  
Ionic Liquid ◽  
Green Synthesis ◽  
Carbonyl Compounds ◽  
Catalytic Effect ◽  
Knoevenagel Condensation ◽  
Solvent Free ◽  
Detailed Mechanism ◽  
Solvent Free Conditions ◽  
First Time ◽  
Task Specific Ionic Liquid

2-Hydroxyethylammonium formate acts as a task-specific ionic liquid (TSIL) for the Knoevenagel condensation of carbonyl compounds with rhodanine to afford arylalkylidene rhodanines under solvent-free conditions and in good-to-excellent yields. Additionally, compared with those in organic solvents, the yields obtained in the presence of our ionic liquid (IL) were significantly increased. The detailed mechanism of the catalytic effect of TSIL is also reported for the first time.

scholarly journals A Solvent-Free Protocol for the Green Synthesis of 5-Arylidene-2,4-thiazolidinediones Using Ethylenediamine Diacetate as Catalyst

2012 ◽  
Vol 2012 ◽  
pp. 1-5 ◽  
Author(s):  
Yuliang Zhang ◽  
Zhongqiang Zhou
Keyword(s):  
Knoevenagel Condensation ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Reusable Catalyst ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Solvent Free Conditions ◽  
High Yields ◽  
Work Up ◽  
Solvent Free Reaction

A simple and efficient synthesis of 5-arylidene-2,4-thiazolidinediones by the Knoevenagel condensation of aromatic aldehydes with 2,4-thiazolidinedione catalyzed by ethylenediamine diacetate under solvent-free conditions is described. The major advantages of this method are simple experimental and work-up procedures, solvent-free reaction conditions, small amount of catalyst, short reaction time, high yields, and utilization of an inexpensive and reusable catalyst.

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