Synthesis of substituted pyrano[3,2-c]pyridines via Diels-Alder reaction of 3-methylenepyridin-4-one

被引：8
|
作者：
Tchabanenko, K [1 ]
Taylor, MGO [1 ]
Adlington, RM [1 ]
Baldwin, JE [1 ]
机构：
[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 01期
关键词：
D O I：
10.1016/j.tetlet.2005.10.119
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
On heating, the di-Boe-pyridin-4-one derivative 7 gave an unstable 3-methylenepyridin-4-one intermediate 3, which underwent a rearomatising Diels-Alder cycloaddition with activated alkenes to give substituted pyrano[3,2-c]pyridines in moderate yields. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：39 / 41
页数：3
相关论文
共 50 条
  • [1] Lanthanide chloride catalyzed imino Diels-Alder reaction.: One-pot synthesis of pyrano[3,2-c]- and furo[3,2-c] quinolines
    Ma, Y
    Qian, CT
    Xie, MH
    Sun, J
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17): : 6462 - 6467
  • [2] Copper(II) bromide-catalyzed imino Diels-Alder reaction:: Synthesis of pyrano[3,2-c]- and furo[3,2-c]tetrahydroquinolines
    Semwal, A
    Nayak, SK
    SYNTHETIC COMMUNICATIONS, 2006, 36 (02) : 227 - 236
  • [3] Lanthanide chloride catalyzed imino Diels-Alder reaction. One-pot synthesis of pyrano[3,2c]- and Furo[3,2-c]quinolines
    Ma, Yun
    Qian, Changtao
    Xie, Meihua
    Sun, Jie
    Journal of Organic Chemistry, 64 (17): : 6462 - 6467
  • [4] Synthesis of furo[3,2-c]- and pyrano[3,2-c]quinolines by lanthanide triflate catalyzed imino-Diels-Alder reaction
    Ma, Y
    Qian, CT
    Xie, MH
    Sun, J
    CHINESE JOURNAL OF CHEMISTRY, 2000, 18 (03) : 377 - 383
  • [5] Synthesis of furo[3,2-c]- and pyrano[3,2-c]quinolines by lanthanide triflate catalyzed imino-Diels-Alder reaction
    马云
    钱长涛
    谢美华
    孙杰
    ChineseJournalofChemistry, 2000, (03) : 377 - 383
  • [6] SYNTHESIS OF CIS OR TRANS 4-HETEROAROMATIC SUBSTITUTED FURANO AND PYRANO[3,2-c]TETRAHYDROQUINOLINES BY ONE-POT IMINO DIELS-ALDER REACTIONS
    Zhou, Rui
    Huang, Wei
    Ren, Wen
    Guo, Li
    Zeng, Shi
    Liu, Pan
    Ouyang, Liang
    Song, Xiangrong
    Peng, Cheng
    He, Gu
    HETEROCYCLES, 2013, 87 (12) : 2495 - 2500
  • [7] Synthesis of Pyrano[3,2-c]pyridines Derivatives
    Jirandehi, H. Fathinejad
    Mirzaiean, M.
    ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (07) : 3168 - 3170
  • [8] VCl3 catalyzed aza-Diels-Alder reaction:: one-pot synthesis of pyrano[3,2-c]quinolines and furo[3,2-c]quinolines
    Sabitha, Gowravaram
    Reddy, M. Shashi Kumar
    Arundhathi, K.
    Yadav, J. S.
    ARKIVOC, 2006, : 153 - 160
  • [9] Imino Diels-Alder adducts.: II.: Two pyrano[3,2-c]quinolines
    Ravikumar, K
    Sridhar, B
    Mahesh, M
    Reddy, VVN
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O267 - O269
  • [10] T3P-A Novel Catalyst for Aza-Diels-Alder Reaction: One-Pot Synthesis of Pyrano [3,2-c]quinolines and furano[3,2-c]quinolines
    Prasanna, T. S. R.
    Raju, K. Mohana
    E-JOURNAL OF CHEMISTRY, 2011, 8 : S420 - S424
12345