Knoevenagel Condensation Reactions of Cyano Malononitrile-Derivatives Under Microwave Radiation

Реакции конденсации Кнёвенагеля цианомалонодинитрильных производных под действием микроволнового излучения
André Luiz Meleiro Porto, David Esteban Quintero Jimenez, Lucas Lima Zanin, Luís P. Fonseca
2018-02-20

Knoevenagel condensationcyanoacetamides and cyanoacetatesgreen chemistrymalononitrile derivativesmicrowave radiation
Knoevenagel condensation was discovered in the 20th century, and since then it has been present in a wide range of reactions in organic chemistry due to its potential for forming carbon-carbon bonds. This reaction is usually carried out between aldehydes or ketones and active methylene compounds in the presence of Lewis acids or basic catalysts. The great advantage of this reaction is that can be carried out in mild conditions, with easy handling and using solvents with low toxicity. In the last 15 years, this type of organic synthesis has been used for the formation of α,β- unsaturated carbonyl compounds according to the principles of Green Chemistry. The use of microwave radiation to perform Knoevenagel condensation reactions is today a reality due to their ability to reduce the reaction time from hours to minutes, absence of unwanted products and free-solvent reactions. In this article we will review and discuss a collection of these reactions under microwave radiation dividing it into two strands. The first presents the condensation of Knoevenagel between malononitrile and aldehydes and the second one, addresses the alternatives to use malononitrile-derivatives such as cyanoacetamides and cyanoacetates. The Knoevenagel adducts formed from aldehydes present excellent results in terms of reaction yield (above 90 %) in short reaction times (
1
Knoevenagel adducts formed from aldehydes generally achieve excellent yields above 90% in short reaction times.
2
Microwave irradiation can reduce Knoevenagel reaction times from hours to minutes while enabling solvent-free conditions and minimizing unwanted products.
3
The review examines Knoevenagel condensation reactions performed under microwave radiation as a Green Chemistry approach.
4
The reviewed reactions are organized into condensation of malononitrile with aldehydes and reactions using derivatives such as cyanoacetamides and cyanoacetates.

Knoevenagel condensation reactions of malononitrile and its derivatives with aldehydes under microwave radiation

Reaction performance, including yield, reaction time, solvent-free operation, and formation of unwanted products, in microwave-assisted Knoevenagel condensations

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2018-02-20
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André Luiz Meleiro Porto
David Esteban Quintero Jimenez
Lucas Lima Zanin
Luís P. Fonseca
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