Synthesis of Diels–Alder adducts of N-arylmaleimides by a multicomponent reaction between maleic anhydride, dienes, and anilines |
| |
Authors: | J Alberto Guevara-Salazar Delia Quintana-Zavala Hugo A Jiménez-Vázquez and José Trujillo-Ferrara |
| |
Institution: | (1) Departamento de Qu?mica Org?nica, Escuela Nacional de Ciencias Biol?gicas, Instituto Polit?cnico Nacional, Prol. Carpio y Plan de Ayala s/n, 11340 Mexico, DF, Mexico;(2) Laboratorio de Qu?mica Org?nica, Centro de Investigaci?n en Ciencia Aplicada y Tecnolog?a Avanzada, Instituto Polit?cnico Nacional, Calzada Legaria No. 694, 11500 Mexico, DF, Mexico;(3) Departamento de Bioqu?mica, Escuela Superior de Medicina, Instituto Polit?cnico Nacional, Salvador D?az Mir?n y Plan de San Luis s/n, 11340 Mexico, DF, Mexico; |
| |
Abstract: | Abstract We have carried out the synthesis and characterization of some hexahydroisoindolyl benzoic acids and their corresponding ethyl
esters by a multicomponent reaction (MCR) between aminobenzoic acids or aminobenzoates, maleic anhydride, and isoprene in
the absence of catalysts. According to additional experiments, the MCR takes place by sequential formation of N-arylmaleamic acids from the aminobenzoic acids or aminobenzoates and maleic anhydride, Diels–Alder adducts of the acids and
isoprene, and finally the imides. The 1H NMR data (coupling constants) of the adducts suggested that the preferred conformation of the corresponding cyclohexene
rings is a syn-boat, a fact supported by a density functional theory (DFT) conformational analysis and DFT calculations of the spin–spin
coupling constants of the corresponding conformers. Our MCR synthetic methodology was tested successfully in the synthesis
of other adducts, for which cyclopentadiene and other anilines were employed. |
| |
Keywords: | |
本文献已被 SpringerLink 等数据库收录! |
|