Ligia S. da Silveira Pinto and Marcus V. N. de Souza* Pages 104 - 107 ( 4 )
This study describes a new, simple and efficient process for the preparation of N-(2- hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide, on a multigram scale (0.38 moles), by using ultrasound irradiation as green chemistry method. Optimal conditions and yield (83%) were obtained by using 1.2 molar equivalents of ethanolamine at 675 W for 5.0 hours. This intermediate is very versatile and could be transformed in a wide range of derivatives, which could be employed in different areas, such as inorganic complexes, dyes, pesticides and fluorescent coumarins. In the medicinal chemistry, N-(2-hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide is also very useful because a wide variety of compounds could be synthesized and evaluated with diverse types of diseases. In this context, it can be mentioned N-(2-chloroethyl)-2-oxo-2H-chromene-3-carboxamide, a useful intermediate, which was synthesized in this work in gram scale (0.04 moles) in 80% of yield, that could react with diverse types of nucleophiles.
Green chemistry, sonochemistry, ultrasound, multigram, coumarin, intermediate.
Departamento de Quimica Organica, Instituto de Quimica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Instituto de Tecnologia em Farmacos-Far-Manguinhos, FioCruz-Fundacao Oswaldo Cruz, Rio de Janeiro