A novel access to highly functionalised β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction

被引：32
|
作者：
Arumugam, N [1 ]
Jayashankaran, J [1 ]
Manian, RDRS [1 ]
Raghunathan, R [1 ]
机构：
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
来源：
TETRAHEDRON | 2005年 / 61卷 / 35期
关键词：
cycloaddition; beta-lactam; azomethine ylide;
D O I：
10.1016/j.tet.2005.06.029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly regio- and stereoselective synthesis of novel spiro containing beta-lactam and oxazolone moieties under two different conditions is achieved using [3 + 2] cycloaddition methodoly in moderate to good yield. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8512 / 8516
页数：5
相关论文
共 50 条
  • [31] 1,3-DIPOLAR CYCLOADDITION REACTION OF AZIRIDINEDICARBOXIMIDE
    OIDA, S
    OHKI, E
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1968, 16 (04) : 764 - +
  • [32] Regio- and stereoselective synthesis of dispirooxindole-pyrrolocarbazole hybrids via 1,3-dipolar cycloaddition reactions: Cytotoxic activity and SAR studies
    Murali, Karunanidhi
    Sparkes, Hazel A.
    Prasad, Karnam Jayarampillai Rajendra
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 : 292 - 305
  • [33] Regio- and facial-selective effects of allylic heteroatoms in 1,3-dipolar cycloaddition of a nitrile oxide
    Kakisawa, Hiroshi, 1600, Chemical Society of Japan (63):
  • [34] Novel synthesis of pyrroloquinolizidines via a 1,3-dipolar cycloaddition reaction
    Qian, Xuelei
    Angle, Steven R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [35] Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: Synthesis of trihalomethylated spiroindenepyrroli(zi)dines
    Barkov, Alexey Yu.
    Zimnitskiy, Nikolay S.
    Kutyashev, Igor B.
    Korotaev, Vladislav Yu.
    Moshkin, Vladimir S.
    Sosnovskikh, Vyacheslav Ya.
    JOURNAL OF FLUORINE CHEMISTRY, 2017, 204 : 37 - 44
  • [36] Antimycobacterial activity of spirooxindolo-pyrrolidine, pyrrolizine and pyrrolothiazole hybrids obtained by a three-component regio- and stereoselective 1,3-dipolar cycloaddition
    Rajesh, Stephen Michael
    Perumal, Subbu
    Carlos Menendez, J.
    Yogeeswari, Perumal
    Sriram, Dharmarajan
    MEDCHEMCOMM, 2011, 2 (07) : 626 - 630
  • [37] First 1,3-dipolar cycloaddition of azomethine ylides with (E)-ethyl 3-fluoroacrylate:: Regio- and stereoselective synthesis of enantiopure fluorinated prolines
    Bonini, BF
    Boschi, F
    Franchini, MC
    Fochi, M
    Fini, F
    Mazzanti, A
    Ricci, A
    SYNLETT, 2006, (04) : 543 - 546
  • [38] Synthesis of novel isoxazoline-fused cyclic β-amino esters by regio- and stereo-selective 1,3-dipolar cycloaddition
    Nonn, Melinda
    Kiss, Lorand
    Forro, Eniko
    Mucsi, Zoltan
    Fueloep, Ferenc
    TETRAHEDRON, 2011, 67 (22) : 4079 - 4085
  • [39] Regio- and stereoselectivity of aromatic and heteroaromatic nitrilimines in 1,3-dipolar cycloadditions
    Jedlovská, E
    Fisera, L
    Liptaj, T
    CHEMICAL PAPERS, 2005, 59 (5-6) : 354 - 361
  • [40] Regio- and stereoselective synthesis of novel spiropyrrolidines through 1,3-dipolar cycloaddition reactions of azomethine ylides and 2-styrylquinazolin-4(3H)-ones
    Maurya, Ram Awatar
    Nayak, Ranjita
    Reddy, Chada Narsimha
    Kapure, Jeevak Sopanrao
    Nanubolu, Jagadeesh Babu
    Singarapu, Kiran Kumar
    Ajitha, M.
    Kamal, Ahmed
    RSC ADVANCES, 2014, 4 (61): : 32303 - 32311
12345