Simple approach to β-lactam derivatives from N-acylimidazoles

被引:53
作者
Nahmany, Moshe [1 ]
Melman, Artem [1 ]
机构
[1] Hebrew Univ Jerusalem, IL-91904 Jerusalem, Israel
关键词
D O I
10.1021/jo0607010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of N-acylimidazoles possessing an electron-withdrawing group in the alpha position with diarylimines produces beta-lactams in high yields.
引用
收藏
页码:5804 / 5806
页数:3
相关论文
共 44 条
[1]   β-lactams as versatile synthetic intermediates for the preparation of heterocycles of biological interest [J].
Alcaide, B ;
Almendros, P .
CURRENT MEDICINAL CHEMISTRY, 2004, 11 (14) :1921-1949
[2]   HYDRATION REACTIVITY OF KETENES GENERATED BY FLASH-PHOTOLYSIS [J].
ALLEN, AD ;
KRESGE, AJ ;
SCHEPP, NP ;
TIDWELL, TT .
CANADIAN JOURNAL OF CHEMISTRY, 1987, 65 (08) :1719-1723
[3]   Highly enantioselective construction of the key azetidin-2-ones for the synthesis of carbapenem antibiotics via intramolecular C-H insertion reactions of α-methoxycarbonyl-α-diazoacetamides catalysed by chiral dirhodium(II) carboxylates [J].
Anada, M ;
Watanabe, N ;
Hashimoto, S .
CHEMICAL COMMUNICATIONS, 1998, (15) :1517-1518
[4]   Mn(III)-promoted sulfur-directed 4-exo-trig radical cyclization of enamides to β-lactams [J].
Attenni, B ;
Cerreti, A ;
D'Annibale, A ;
Resta, S ;
Trogolo, C .
TETRAHEDRON, 1998, 54 (39) :12029-12038
[5]   A carbene insertion route to β-lactam fused cyclic enediynes [J].
Basak, A ;
Mandal, S .
TETRAHEDRON LETTERS, 2002, 43 (23) :4241-4243
[6]   ACIDITIES OF SULFOXIMINES AND RELATED OXOSULFONIUM CATIONS - CYCLOPROPYL EFFECTS AND STRUCTURES OF ALPHA-SULFONYL-TYPE CARBANIONS [J].
BORDWELL, FG ;
BRANCA, JC ;
JOHNSON, CR ;
VANIER, NR .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (19) :3884-3889
[7]   LIGAND EFFECTS IN THE RHODIUM(II)-CATALYZED REACTIONS OF ALPHA-DIAZOAMIDES - OXINDOLE FORMATION IS PROMOTED BY THE USE OF RHODIUM(II) PERFLUOROCARBOXAMIDE CATALYSTS [J].
BROWN, DS ;
ELLIOTT, MC ;
MOODY, CJ ;
MOWLEM, TJ ;
MARINO, JP ;
PADWA, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2447-2455
[8]   HYDROLYSIS OF ESTERS AND AMIDES IN STRONGLY BASIC SOLUTION - EVIDENCE FOR THE INTERMEDIACY OF CARBANIONS [J].
BROXTON, TJ ;
DUDDY, NW .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06) :1186-1191
[9]  
Bryskier A, 2005, ANTIMICROBIAL AGENTS: ANTIBACTERIALS AND ANTIFUNGALS, P113
[10]  
Cheong D.Y., 1992, J KOREAN CHEM SOC, V36, P446