Solventless Lactam Synthesis by Intramolecular Cyclizations of α-Iminoester Derivatives under Microwave Irradiation 英文参考文献.docVIP

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Solventless Lactam Synthesis by Intramolecular Cyclizations of α-Iminoester Derivatives under Microwave Irradiation 英文参考文献.doc

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Solventless Lactam Synthesis by Intramolecular Cyclizations of α-Iminoester Derivatives under Microwave Irradiation 英文参考文献

Molecules 2007, 12, 439-454 molecules ISSN 1420-3049 Full Paper Solventless Lactam Synthesis by Intramolecular Cyclizations of α-Iminoester Derivatives under Microwave Irradiation Fatima-Zohra Zradni 1,*, Jack Hamelin 2 and Aicha Derdour 1,? 1 Faculté des Sciences, Département de Chimie, Université d’Es-sénia, Oran, B.P 1524, Algeria; ?E-Mail: derdouraicha@yahoo.fr 2 Groupe dIngénierie Chimique et Molécules pour le Vivant 3(ICMV3)-UMR 6226, Université de Rennes 1, Campus de Beaulieu, 35042 Rennes, France; E-mail: jack.hamelin@orange.fr * Author to whom correspondence should be addressed; E-mail: fzradnidz@yahoo.fr; Tel/Fax: (+213) 41 58 70 57 Received: 27 January 2007; in revised form: 17 February 2007 / Accepted: 7 March 2007 / Published: 12 March 2007 Abstract: We have previously reported a new synthesis of amides from esters and amines under microwave irradiation, offering much higher yields than those achieved with conventional heating [1]. We have now extended these studies to the ring closure of neat iminoesters I2, I3 and I4-I6 to give five- and six-membered ring lactams L5, L6 and larger lactams L7-L9 (where I means imine and L means lactam), respectively, under both classical heating conditions and microwave irradiation. Keywords: Medium-sized ring lactams; imine alkylation; Schiff bases; microwave irradiation. Introduction Lactams are of considerable interest in a number of areas, ranging from drug discovery to the polymer industry, and consequently their synthesis has been, and still is, a topic of significant interest for organic chemists. Among the numerous methods developed radical strategies [2], especially intramolecular cyclizations of unsaturated α-carbamoyl radicals [3,4] or in our case imines, have been Molecules 2007, 12 440 shown to be some of the best tools for the construction of a variety of lactam skeletons ranging from β- lactams to medium- or larger sized one