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SYNTHESE CASCADE EN MILIEU BASIQUE DE LACTONES. APPLICATION A LA SYNTHESE DE LA CERPEGINE ET D'ISOBENZOFURANONES


VILLEMIN DIDIER 1, LIANG LIAO 1, BAR NATHALIE 1, CHEIKH NAWEL 2, MOSTEFA-KARA BACHIR 2, CHOUKCHOU-BRAHAM NOUREDDINE 2, DIDI MOHAMED A. 2
(1)ENSICAEN, LCMT - UMR 6507 CNRS, UNIVERSITÉ DE CAEN, 14050 CAEN, FRANCE (2)LABORATOIRE DE CATALYSE, UNIVERSITÉ DE TLEMCEN, BP 119, TLEMCEN, ALGÉRIE

Issue:

SCSCC6, Volume VII, No. 4

Section:

Volume VII, No. 4 (2006)

Abstract:

New cascade synthesis (domino synthesis) of butenolides starting from alpha hydroxyketones are described by using environmental friendly procedures. The butenolides esters and nitriles are obtained by cascade reactions of Dreux without solvent and under microwaves irradiation. The reaction was generalized with the synthesis of butenolides carrying a sulfenyle group, sulfoxide, sulfone and phosphoryl. By using BMIM, BF4 as ionic liquid, it is possible to make the synthesis with a good yield, while recycling the ionic liquid and the base. This reaction of Dreux was used for the domino synthesis of the alkaloid Cerpegine in a one-pot domino reaction. This domino synthesis allows the convergent and fast synthesis of a great number of analogues of Cerpegine. Finally a new synthesis without solvent and under microwaves irradiation of isobenzofuranones was discovered. This synthesis brings into play five successive cascade reactions starting from alpha hydroxyketone.

Keywords:

domino reactions, parallel reactions, butenolides, natural products, pharmacology.

Code [ID]:

CSCC6200607V04S01A0023 [0001601]

Full paper:

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