Synthesis of novel 4-(5′-pyrrolidinyl)-β-lactams

被引:45
|
作者
Grigg, R [1 ]
Thornton-Pett, M [1 ]
Xu, J [1 ]
Xu, LH [1 ]
机构
[1] Univ Leeds, Sch Chem, Mol Innovat Divers & Automated Synth Ctr, Leeds LS2 9JT, W Yorkshire, England
关键词
beta-lactams; azomethine ylide; cycloaddition; cascade reaction;
D O I
10.1016/S0040-4020(99)00867-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of novel 4-(5'-pynolidinyl)-beta-lactams from imines derived from 4-formyl-beta-lactams and alpha-amino esters via cascade imine-->azomethine ylide-->1,3-dipolar cycloaddition reactions is described. These cascades are endo-specific, exhibit facial stereoselectivity and occur in good to excellent yields. (C) 1999 Elsevier Science Ltd. Ail rights reserved.
引用
收藏
页码:13841 / 13866
页数:26
相关论文
共 50 条
  • [32] Synthesis of Some Novel 4-(Furan-2-yl)-5,6-dimethylpyridines
    Gouda, Moustafa A.
    Berghot, Moged A.
    Abd El-Ghani, Ghada E.
    Khalil, Abd El-Galil M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (08) : 1935 - 1941
  • [34] Toward novel glyconjugates:: Efficient synthesis of glycosylated 4-alkylidene-β-lactams
    Adinolfi, M
    Galletti, P
    Giacomini, D
    Iadonisi, A
    Quintavalla, A
    Ravidà, A
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) : 69 - 73
  • [35] 5-(2-Pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes: Synthesis of all the stereoisomers and α4β2 nicotinic affinity
    Pallavicini, Marco
    Bolchi, Cristiano
    Binda, Matteo
    Cilia, Antonio
    Clementi, Francesco
    Ferrara, Rossana
    Fumagalli, Laura
    Gotti, Cecilia
    Moretti, Milena
    Pedretti, Alessandro
    Vistoli, Giulio
    Valoti, Ermanno
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (03) : 854 - 859
  • [36] A general and versatile synthesis of 4- and 5-oxoacids
    Lhommet, G
    Freville, S
    Thuy, V
    Petit, H
    Celerier, JP
    SYNTHETIC COMMUNICATIONS, 1996, 26 (21) : 3897 - 3901
  • [38] 4-(pyrrolidinyl)methoxybenzoic acid derivatives as a potent, orally active VLA-4 antagonist
    Chiba, Jun
    Iimura, Shin
    Yoneda, Yoshiyuki
    Sugimoto, Yuichi
    Horiuchi, Takao
    Muro, Fumito
    Ochiai, Yuichi
    Ogasawara, Tomomi
    Tsubokawa, Masao
    Iigou, Yutaka
    Takayama, Gensuke
    Taira, Tomoe
    Takata, Yoshimi
    Yokoyama, Mika
    Takashi, Tohru
    Nakayama, Atsushi
    Machinaga, Nobuo
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (11) : 1515 - 1529
  • [39] Synthesis of 4-dendronized β-lactams
    Díez-Barra, E
    García-Martínez, JC
    Rodríguez-López, J
    SYNLETT, 2003, (11) : 1587 - 1590
  • [40] Synthesis and Herbicidal Activities of Novel 4-(4-(5-methyl-3-arylisoxazol-4-yl)thiazol-2-yl)piperidyl Carboxamides and Thiocarboxamides
    Hu, De-Jin
    Liu, Su-Fang
    Huang, Tong-Hui
    Tu, Hai-Yang
    Zhang, Ai-Dong
    MOLECULES, 2009, 14 (03) : 1288 - 1303