ADDITION OF AMINO LACTAMS TO VINYL VICINAL TRICARBONYLS - FORMATION OF TRICYCLIC 2-AZADETHIAPENAMS AND 3-AZADETHIACEPHAMS

被引:29
作者
WASSERMAN, HH [1 ]
HENKE, SL [1 ]
LUCE, P [1 ]
NAKANISHI, E [1 ]
SCHULTE, G [1 ]
机构
[1] YALE UNIV,YALE INSTRUMENT CTR,NEW HAVEN,CT 06511
关键词
D O I
10.1021/jo00310a012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amino lactams react as trinucleophiles with vinyl vicinal tricarbonyl esters to form tricyclic derivatives. Products of particular interest resulting from this reaction sequence are 2-azadethiapenams and 3-azadethiacephams. © 1990, American Chemical Society. All rights reserved.
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页码:5821 / 5823
页数:3
相关论文
共 21 条
[1]   THE HYDROGENATION OF ESTERS TO ALCOHOLS AT 25-DEGREES-150-DEGREES [J].
ADKINS, H ;
BILLICA, HR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (09) :3121-3125
[2]   THIENAMYCIN TOTAL SYNTHESIS .1. SYNTHESIS OF AZETIDINONE PRECURSORS OF (+/-)-THIENAMYCIN AND ITS STEREOISOMERS [J].
BOUFFARD, FA ;
JOHNSTON, DBR ;
CHRISTENSEN, BG .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) :1130-1135
[3]   SYNTHESIS OF NOVEL FUSED BETA-LACTAMS BY INTRAMOLECULAR 1,3-DIPOLAR CYCLO-ADDITIONS .7. (9RS,9ARS)-9,9A-DIHYDRO-5-METHYL-8-OXO-9-PHENOXYACETAMIDO-8H-AZETO[1,2-A]-V-TRIAZOLO[5,1-C]PYRAZINE-6-CARBOXYLIC ACIDS AND (3BRS,4RS,7SR)-4,5-DIHYDRO-5-OXO-4-PHENOXYACETAMIDO-3BH-AZETO[1',2'-3,4]-IMIDAZO[1,5-C]-V-TRIAZOLE-7-CARBOXYLIC ACID, [J].
BRANCH, CL ;
FINCH, SC ;
PEARSON, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07) :1491-1498
[4]   SYNTHESIS OF NOVEL FUSED BETA-LACTAMS BY INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITIONS .9. PREPARATION OF THE 7-OXO-1,3-DIAZABICYCLO[3.2.0]-HEPTANE-2-CARBOXYLATE AND 8-OXO-1,3-DIAZABICYCLO[4.2.0]OCTANE-2-CARBOXYLATE RING-SYSTEMS [J].
BRANCH, CL ;
PEARSON, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (06) :1077-1095
[5]  
CHRISTENSEN BG, 1979, Patent No. 4174316
[6]  
CHRISTENSON J, 1989, RECENT ADV CHEM BETA, P33
[8]   NUCLEAR ANALOGS OF BETA-LACTAM ANTIBIOTICS .7. THE SYNTHESIS OF 3-THIA-1-DETHIACEPH-1-EM ESTERS AND 3-AZA-1-DETHIACEPH-1-EM ESTERS [J].
GLEASON, JG ;
BRYAN, DB ;
HOLDEN, KG .
TETRAHEDRON LETTERS, 1980, 21 (41) :3947-3950
[9]   NUCLEAR ANALOGS OF BETA-LACTAM ANTIBIOTICS .1. TOTAL SYNTHESIS OF A 7-OXO-1,3-DIAZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID VIA A VERSATILE MONOCYCLIC BETA-LACTAM INTERMEDIATE [J].
HUFFMAN, WF ;
HOLDEN, KG ;
BUCKLEY, TF ;
GLEASON, JG ;
WU, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) :2352-2353
[10]   A COMPARISON OF THE ANTI-BACTERIAL ANTI-BACTERIAL AND BETA-LACTAMASE INHIBITING PROPERTIES OF PENAM AND (2,3)-BETA-METHYLENEPENAM DERIVATIVES - THE DISCOVERY OF A NEW BETA-LACTAMASE INHIBITOR - CONFORMATIONAL REQUIREMENTS FOR PENICILLIN ANTI-BACTERIAL ACTIVITY [J].
KEITH, DD ;
TENGI, J ;
ROSSMAN, P ;
TODARO, L ;
WEIGELE, M .
TETRAHEDRON, 1983, 39 (15) :2445-2458