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A Green Synthesis and a Chemical Study of the Coumarin, 1-(2-Hydroxy- 2-methyl-2H-chromen-3yl)ethanone

[ Vol. 16 , Issue. 2 ]

Author(s):

Emerson Teixeira da Silva, Ligia Souza da Silveira Pinto, Solange Maria Silva Veloso Wardell, James Lewis Wardell and Marcus Vinícius Nora de Souza*   Pages 128 - 133 ( 6 )

Abstract:


Coumarins are a class of natural and synthetic products with a wide variety of applications in different fields. Due to the general importance of coumarins, the objective of this work is to further develop the chemistry of 1-(2-hydroxy-2-methyl-2H-chromen-3yl)ethanone, 1, a potentially useful and versatile coumarin but an under-reported compound in the literature. This work describes a green preparation of 1 in the absence of solvents and acids, thereby eliminating byproducts, normally obtained in classical procedures, and a mechanistic study of the reactions of 1 with nucleophiles. In addition, we report the characterisation of 1-(2-ethoxy-2-methyl-2H-chromen-3-yl)ethanone 2, via X-ray crystallography and 2D NMR spectra.

Keywords:

Coumarin, green synthesis, X-ray crystallography, sonochemistry, free solvent, heterocycle.

Affiliation:

Instituto de Tecnologia em Farmacos-Farmanguinhos, Fundacao Oswaldo Cruz - Fiocruz, Rio de Janeiro, Instituto de Tecnologia em Farmacos-Farmanguinhos, Fundacao Oswaldo Cruz - Fiocruz, Rio de Janeiro, CHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Department of Chemistry, University of Aberdeen, Old Aberdeen, AB 24 3UE, Instituto de Tecnologia em Farmacos-Farmanguinhos, Fundacao Oswaldo Cruz - Fiocruz, Rio de Janeiro

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