Intramolecular 1,3-dipolar nitrone cycloaddition route to bicyclic fused enediyne

被引:10
|
作者
Basak, A [1 ]
Ghosh, SC [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
enediynes; nitrone cycloaddition; regioselective; Bergman cyclization; Sonogashira coupling;
D O I
10.1016/j.tetlet.2005.08.125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bicyclic isooxazolidinyl enediynes I and 2 have been prepared by intramolecular nitrone cycloaddition between the two arms of an acyclic enediyne precursor 13. The reaction is highly regioselective and the two configurational isomers have similar onset temperatures for BC indicating no influence of bridgehead stereochemistry on the kinetics of cyclization. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:7385 / 7388
页数:4
相关论文
共 50 条
  • [1] Intramolecular 1,3-dipolar cycloaddition of a nitrone to a 1,4-quinone
    Bentley, Sierra
    McMahon, Wayne
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [2] Intramolecular 1,3-dipolar cycloaddition as a route to triazolobenzodiazepines and pyrrolobenzodiazepines
    Chambers, Christopher S.
    Patel, Nilesh
    Hemming, Karl
    TETRAHEDRON LETTERS, 2010, 51 (37) : 4859 - 4861
  • [3] A stereoselective intramolecular 1,3-dipolar nitrone cycloaddition for the synthesis of substituted chromanes
    Zhao, Q
    Han, FS
    Romero, DL
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10): : 3317 - 3322
  • [4] Functionalized azabicycloalkane amino acids by nitrone 1,3-dipolar intramolecular cycloaddition
    Manzoni, L
    Arosio, D
    Belvisi, L
    Bracci, A
    Colombo, M
    Invernizzi, D
    Scolastico, C
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10): : 4124 - 4132
  • [5] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF A HETEROCYCLIC NITRONE
    ALI, SA
    ALMUALLEM, HA
    TETRAHEDRON, 1992, 48 (25) : 5273 - 5282
  • [6] An intramolecular 1,3-dipolar cycloaddition involving one alkyne and two nitrone groups
    Aurich, HG
    Biesemeier, F
    Harms, K
    LIEBIGS ANNALEN-RECUEIL, 1997, (03): : 469 - 471
  • [7] STEREOSELECTIVE INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF CHIRAL CHROMIUM TRICARBONYL COMPLEXED NITRONE
    BALDOLI, C
    DELBUTTERO, P
    LICANDRO, E
    MAIORANA, S
    ALBINATI, A
    TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1711 - 1717
  • [8] Intramolecular 1,3-dipolar cycloaddition of an azidoquinone
    McCabe, Charles
    McMahon, Wayne
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [9] INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTIONS
    PADWA, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1976, 15 (03) : 123 - 136
  • [10] STUDIES ON INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTIONS .2. THE THERMOCHEMICAL AND PHOTOCHEMICAL-REACTIONS OF THE FURAN 1,3-DIPOLAR NITRONE SYSTEM
    CHEN, QH
    WANG, XL
    ACTA CHIMICA SINICA, 1987, 45 (04) : 340 - 343