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Current Organic Chemistry

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Research Article

Sustainable Synthesis of Benzylidenemalononitrile Compounds Under Microwave- Irradiation

Author(s): David E.Q. Jimenez, Lucas L. Zanin, Irlon M. Ferreira, Victor M. Deflon, Luan F. Diniz, Javier Ellena, Roberto L.A. Haiduke and André L. M. Porto*

Volume 26, Issue 16, 2022

Published on: 21 December, 2022

Page: [1552 - 1564] Pages: 13

DOI: 10.2174/1385272827666221125091631

Price: $65

Abstract

A green methodology was developed to obtain a large scope of Knoevenagel adducts with high yields (77-95%). The compounds were synthetized in 30 min, using aromatic aldehyde derivatives, malononitrile, water as a solvent, microwave irradiation as a heating source and in free-catalyst conditions. In a particular case, in the synthesis of the adduct derived from the α-methyl-trans-cinnamaldehyde, a [2+2] photochemical cycloaddition product was observed, a tetrasubstituted cyclobutane dimeric compound 3w’. Its complex structure was confirmed by X-ray diffraction (first time), nuclear magnetic resonance analysis and electronic structure calculations. Theoretical results suggest that the thermal decomposition of 3w’ back to 3w can occur by means of a biradical intermediate.

Keywords: Microwave irradiation, X-ray diffraction, knoevenagel adducts, [2+2] cycloaddition, photochemical reaction, green chemistry.

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