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Green Synthetic Methodology of (E)-2-cyano-3-aryl Selective Knoevenagel Adducts Under Microwave Irradiation

[ Vol. 6 , Issue. 1 ]

Author(s):

David Esteban Quintero Jimenez, Lucas Lima Zanin, Luan Farinelli Diniz, Javier Ellena and AndrĂ© Luiz Meleiro Porto*   Pages 54 - 60 ( 7 )

Abstract:


Background: The Knoevenagel condensation is an important reaction in organic chemistry because of its capacity to form new C-C bonds and its products are mainly used in organic synthesis as intermediates, due to the large number of reactions they can undergo. Based on the importance of the Knoevenagel adducts, a sustainable synthetic methodology was developed employing microwave irradiation.

Objective: Develop a synthetic methodology employing microwave irradiation and green solvents to obtain Knoevenagel adducts with high yields.

Methods: Knoevenagel condensation reactions were evaluated with different basic catalysts, as well as in the presence or absence of microwave irradiation. The scope of the reaction was expanded using different aldehydes, cyanoacetamide or methyl cyanoacetate. The geometry of the formed products was also evaluated.

Results: After the optimization process, the reactions between aldehydes and cyanoacetamide were performed with triethylamine as catalyst, in the presence of microwave irradiation, in 35 minutes, using NaCl solution as solvent and resulted in high yields 90-99%. The reactions performed between aldehydes and methyl cyanoacetate were also performed under these conditions, but showed better yields with EtOH as solvent 70-90%. Finally, from X-ray analysis, the (E)-geometry of these compounds was confirmed.

Conclusion: In this study we developed synthetic methodology of Knoevenagel condensation using triethylamine, green solvents and microwave irradiation. In 35 minutes, products with high yields (70- 99%) were obtained and the (E)-geometry of the adducts was confirmed.

Keywords:

Aldol reaction, cyanoacetamide, methyl cyanoacetate, crystallographic structures, knoevenagel condensation, microwave.

Affiliation:

Laboratorio de Quimica Organica e Biocatalise, Instituto de Quimica de Sao Carlos, Universidade de Sao Paulo, Av. Joao Dagnone, 1100, Ed. Quimica Ambiental, Santa Angelina, 13563-120, Sao Carlos, Sao Paulo, Laboratorio de Quimica Organica e Biocatalise, Instituto de Quimica de Sao Carlos, Universidade de Sao Paulo, Av. Joao Dagnone, 1100, Ed. Quimica Ambiental, Santa Angelina, 13563-120, Sao Carlos, Sao Paulo, Laboratorio Multiusuario de Cristalografia Estrutural, Instituto de Fisica de Sao Carlos, Universidade de Sao Paulo, Av. Trabalhador Sao-carlense, 400, Parque Arnold Schimidt, 13566-590, Sao Carlos, Sao Paulo, Laboratorio Multiusuario de Cristalografia Estrutural, Instituto de Fisica de Sao Carlos, Universidade de Sao Paulo, Av. Trabalhador Sao-carlense, 400, Parque Arnold Schimidt, 13566-590, Sao Carlos, Sao Paulo, Laboratorio de Quimica Organica e Biocatalise, Instituto de Quimica de Sao Carlos, Universidade de Sao Paulo, Av. Joao Dagnone, 1100, Ed. Quimica Ambiental, Santa Angelina, 13563-120, Sao Carlos, Sao Paulo

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