Can I read Intramolecular Versus Intermolecular Diels-alder Reaction In The Cyclisation Reaction Of Furfuryl Amines With Maleic Anhydride on EtoBox?

Intramolecular Versus Intermolecular Diels-alder Reaction In The Cyclisation Reaction Of Furfuryl Amines With Maleic Anhydride by Pierre BRUN; Jean ZYLBER; Gerard PEPE; Jean-Pierre REBOUL is a Chemistry article available to read on EtoBox.

What is Intramolecular Versus Intermolecular Diels-alder Reaction In The Cyclisation Reaction Of Furfuryl Amines With Maleic Anhydride about?

The mechanism of the reaction between various N-substituted furfuryl amines and maleic anhydride was re-investigated and fully elucidated. The reaction proceeds by condensation of the amino group on the anhydride function followed by an intramolecular Diels-Alder reaction. In one case the intermediate compound was isolated and fully characterized for the first time. Intramolecular Diels-Alder (IMDA) reactions of furan derivatives offer a very fruitful entry to the synthesis of substituted heterocycles (1, 2, 3, 4, 5 ). In connection with a work directed to the synthesis of optically active γ lactams (figure 1) we re-examined the mechanism of the cyclization of furfuryl amines with maleic anhydride and the structure of the adduct for which two different stereoisomers have been proposed (6, 7). Two different pathways may account for the cyclization reaction (figure 2): -condensation of the amine 1 with maleic anhydride 2, followed by an IMDA reaction (path A) -intermolecular Diels-Alder reaction (NDA) of the furan nucleus with 2, followed by an intramolecular attack of the amino group on the anhydride function (path B).

Who reads Intramolecular Versus Intermolecular Diels-alder Reaction In The Cyclisation Reaction Of Furfuryl Amines With Maleic Anhydride?

Author

Pierre BRUN; Jean ZYLBER; Gerard PEPE; Jean-Pierre REBOUL

Publisher

Walter de Gruyter GmbH

Published

1994

Language

EN

Field

Chemistry (Physical Sciences)