PREPARATION OF ALPHA-METHYLENE AND ALPHA-ETHYLIDENE BETA-LACTAMS VIA THE ESTER ENOLATE IMINE CONDENSATION USING BETA-(DIALKYLAMINO) ESTERS AS STARTING MATERIALS - SCOPE AND SYNTHETIC APPLICATIONS

被引：36

作者：

ALCAIDE, B ^{[1
]}

ESTEBAN, G ^{[1
]}

MARTINCANTALEJO, Y ^{[1
]}

PLUMET, J ^{[1
]}

RODRIGUEZLOPEZ, J ^{[1
]}

MONGE, A ^{[1
]}

PEREZGARCIA, V ^{[1
]}

机构：

[1] UNIV COMPLUTENSE MADRID,FAC QUIM,DIFRACC RAYOS X LAB,E-28040 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 26期

关键词：

D O I：

10.1021/jo00105a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, simple procedure for the preparation of appropriately substituted alpha-methylene and alpha-ethylidene beta-lactams via the ester enolate-imine condensation is described. The method is based on the use of lithium 3-(dialkylamino) ester enolates as synthetic equivalents of the corresponding acrylate alpha-anions. Thus, the reaction of lithium enolates of 3-(dialkylamino) esters with imines produced alpha-[(dialkylamino)alkyl] beta-lactams stereoselectively and in high yield. Upon dehydroamination the latter furnished a variety of alpha-alkylidene beta-lactams. The synthesis of 3-alkylidene-4-formyl-2-azetidinones is a particularly significant feature of this work. Preparation of functionalized alpha-keto beta-lactams and beta-lactam-furan hybrids through a dihydroxylation-oxidation process starting from different alpha-alkylidene derivatives is also described. In addition, reduction of various 4-functionalized (Z)- and (E)-3-ethylidene-2-azetidinones yielded the corresponding 3-ethylideneazetidines as advanced precursors of polyoximic acids.

引用

页码：7994 / 8002

页数：9

共 71 条

[1] NOVEL SYNTHESES OF 3-METHYLENE-AZETIDIN-2-ONE DERIVATIVES AND RELATED SYSTEMS [J].

ADLINGTON, RM ;

BARRETT, AGM ;

QUAYLE, P ;

WALKER, A ;

BETTS, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (09) :404-405

[2]

AGAWA T, 1980, SYNTHESIS-STUTTGART, P933

[3] REGIOCONTROLLED NUCLEOPHILIC-ADDITION TO THE CARBONYL AND IMINO GROUPS IN THE REACTION OF 2-ARYLAMINO-2-METHOXY-1-PHENYLETHANONES WITH SIMPLE LITHIUM ESTER ENOLATES [J].

ALCAIDE, B ;

RODRIGUEZLOPEZ, J ;

MONGE, A ;

PEREZGARCIA, V .

TETRAHEDRON, 1990, 46 (19) :6799-6820

[4] SYNTHESIS OF NOVEL FUNCTIONALIZED MONOCYCLIC 2-AZETIDINONES FROM N,N'-DIARYL-ALPHA-DIIMINES AND LITHIUM ESTER ENOLATES [J].

ALCAIDE, B ;

GOMEZ, A ;

PLUMET, J ;

RODRIGUEZLOPEZ, J .

TETRAHEDRON, 1989, 45 (09) :2751-2762

[5] A NOVEL SYNTHETIC APPROACH TO ALPHA-ALKYLIDENE-BETA-LACTAMS [J].

ALCAIDE, B ;

PLUMET, J ;

RODRIGUEZLOPEZ, J ;

SANCHEZCANTALEJO, YM .

TETRAHEDRON LETTERS, 1990, 31 (17) :2493-2496

[6] THE STEREOSELECTIVE PREPARATION OF MONO-BETA-LACTAMS AND BIS-BETA-LACTAMS BY THE 1,4-DIAZA 1,3-DIENE-ACID CHLORIDE CONDENSATION - SCOPE AND SYNTHETIC APPLICATIONS [J].

ALCAIDE, B ;

MARTINCANTALEJO, Y ;

PEREZCASTELLS, J ;

RODRIGUEZLOPEZ, J ;

SIERRA, MA ;

MONGE, A ;

PEREZGARCIA, V .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5921-5931

[7] A NOVEL, GENERAL, TOTALLY STEREOSELECTIVE ONE-POT SYNTHESIS OF CIS-3-SUBSTITUTED 4-FORMYLAZETIDIN-2-ONES [J].

ALCAIDE, B ;

MARTINCANTALEJO, Y ;

PLUMET, J ;

RODRIGUEZLOPEZ, J ;

SIERRA, MA .

TETRAHEDRON LETTERS, 1991, 32 (06) :803-806

[8] REGIOSPECIFIC SYNTHESIS OF ALPHA-METHYLENE-BETA-LACTAMS BY A HOMOGENEOUS PALLADIUM CATALYZED RING EXPANSION-CARBONYLATION REACTION [J].

ALPER, H ;

HAMEL, N .

TETRAHEDRON LETTERS, 1987, 28 (28) :3237-3240

[9] 6-ACETYLMETHYLENEPENICILLANIC ACID (RO 15-1903), A POTENT BETA-LACTAMASE INHIBITOR .1. INHIBITION OF CHROMOSOMALLY AND R-FACTOR-MEDIATED BETA-LACTAMASES [J].

ARISAWA, M ;

THEN, RL .

JOURNAL OF ANTIBIOTICS, 1982, 35 (11) :1578-1583

[10] STEREOSELECTIVE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS FROM ALPHA-ALKOXY ALDEHYDES [J].

BANFI, L ;

COLOMBO, L ;

GENNARI, C ;

SCOLASTICO, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (19) :1112-1113

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