Lewis acid mediated functionalization of β-lactams:: mechanistic study and synthesis of C-3 unsymmetrically disubstituted azetidin-2-ones

被引:15
|
作者
Bhalla, Arnan [1 ]
Rathee, Suman [1 ]
Madan, Sachin [1 ]
Venugopalan, Paloth [1 ]
Bari, Shamsher S. [1 ]
机构
[1] Panjab Univ, Dept Chem, Chandigarh 160014, India
关键词
azetidin-2-ones; Lewis acid; nucleophiles; monosubstituted beta-lactams; unsymmetrically disubstituted azetidin-2-ones;
D O I
10.1016/j.tetlet.2006.05.160
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and efficient route to novel unsymmetrically disubstituted azetidin-2-ones is described. beta-Lactam carbocation equivalents of type 1 and active aromatic substrates in the presence of a Lewis acid promote a facile and stereoselective C-3 substitution to provide monosubstituted beta-lactams (3,4) and symmetrically disubstituted beta-lactams (5). cis-3-(4'-Methoxyphenyl)3-phenylthioazetidin-2-ones (4) undergo further substitution with active aromatic substrates mediated by a Lewis acid to afford unsymmetrically disubstituted azetidin-2-ones (7). (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5255 / 5259
页数:5
相关论文
共 50 条
  • [21] Synthesis, characterization and antibacterial study of 1-arylamido-3-chloro-4-(2-chloroquinolin-3-yl)-azetidin-2-ones
    Gharad, Spruha A.
    Berad, Baliram N.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2016, 93 (02) : 223 - 228
  • [22] Synthesis of novel 4-(1-ethoxycarbonyl-methylidene)-azetidin-2-ones via a Lewis acid-catalyzed reaction of ethyl diazoacetate
    Cainelli, G
    Galletti, P
    Gazzano, M
    Giacomini, D
    Quintavalla, A
    TETRAHEDRON LETTERS, 2002, 43 (02) : 233 - 235
  • [23] 3-(2-alkoxy-1-hydroxyethyl)azetidin-2-ones: Potential intermediates for the synthesis of novel carbapenems
    O'Leary, AC
    Waldron, CM
    Burke, CM
    Keaveny, RD
    Meegan, MJ
    JOURNAL OF CHEMICAL RESEARCH-S, 1998, (02): : 64 - 65A
  • [24] N/C-4 substituted azetidin-2-ones: Synthesis and preliminary evaluation as new class of antimicrobial agents
    Halve, Arland K.
    Bhadauria, Deepti
    Dubey, Rakesh
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (02) : 341 - 345
  • [25] Triflic acid promoted fries rearrangement of C-3 vinyl/isopropenyl-azetidin-2-ones: single-pot synthesis of C-3 functionalized-2-aryl-2,3-dihydroquinoline-4(1H)-ones
    Mehra, Vishu
    Singh, Parvesh
    Bisetty, Krishna
    Kumar, Vipan
    RSC ADVANCES, 2014, 4 (79) : 41793 - 41801
  • [26] SYNTHESIS OF BETA-LACTAMS OF HIGH ENANTIOMERIC PURITY BY CHIRAL LIGAND ACCELERATED OSMYLATION OF RACEMIC 4-(2-STYRYL)-AZETIDIN-2-ONES
    ANNUNZIATA, R
    BENAGLIA, M
    CINQUINI, M
    COZZI, F
    PONZINI, F
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) : 2397 - 2402
  • [27] STEREOSELECTIVE SYNTHESIS OF AZETIDIN-2-ONES, PRECURSORS OF BIOLOGICALLY-ACTIVE SYN-3-AMINO-2-HYDROXYBUTANOIC ACIDS
    ANNUNZIATA, R
    BENAGLIA, M
    CINQUINI, M
    COZZI, F
    PONZINI, F
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17): : 4746 - 4748
  • [28] STUDIES ON DIPOLAR CYCLOADDITION REACTIONS - SYNTHESIS OF 3,4-DISUBSTITUTED 1-(2,4-DICHLOROBENZAMIDOYL)AZETIDIN-2-ONES AND FUSED DELTA-2-PYRAZOLINES
    SARMA, CS
    GOGOI, PC
    KATAKY, JCS
    HETEROCYCLES, 1990, 31 (01) : 59 - 65
  • [29] Synthetic and Mechanistic Investigations in cis-3-(Substituted acetoxy)azetidin-2-ones from cis-3-Hydroxyazetidin-2-ones: Potential Synthons for Pharmacophoric Hybridized Molecules
    Bhalla, Aman
    Modi, Garima
    Kaur, Jaswinder
    Kumar, Pankaj
    Bari, Shamsher S. S.
    LETTERS IN ORGANIC CHEMISTRY, 2023, 20 (09) : 883 - 891
  • [30] SYNTHESIS OF AZETIDIN-2-ONES DERIVED FROM 7-ACETOXY-3-AMINO-2H-1-BENZOPYRAN-2-ONE
    Ajmeri, A. A.
    Bhanderi, K. D.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 24 (03) : 367 - 370