Isoxazoles from 1,1-disubstituted bromoalkenes

被引:58
|
作者
Dadiboyena, Sureshbabu [1 ]
Xu, Jianping [1 ]
Hamme, Ashton T., II [1 ]
机构
[1] Jackson State Univ, Dept Chem, Jackson, MS 39217 USA
关键词
cycloaddition; regioselectivity; heterocycles; alkyne surrogate; dehydrohalogenation;
D O I
10.1016/j.tetlet.2006.12.005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective synthesis of 3,5-disubstituted isoxazoles was achieved through the 1,3-dipolar cycloaddition of nitrile oxides with 1,1-disubstituted bromoalkenes. The substituted bromoalkenes function as alkyne synthons which were used to construct 5,5-disubstituted bromoisoxazoline intermediates that aromatize to the analogous isoxazoles through the loss of HBr. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1295 / 1298
页数:4
相关论文
共 50 条
  • [31] Asymmetric cobalt catalysts for hydroboration of 1,1-disubstituted alkenes
    Chen, Jianhui
    Xi, Tuo
    Ren, Xiang
    Cheng, Biao
    Guo, Jun
    Lu, Zhan
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (11): : 1306 - 1309
  • [32] DIELS-ALDER ADDUCTS OF 1,1-DISUBSTITUTED OLEFINS
    CANTELLO, BC
    MELLOR, JM
    TETRAHEDRON LETTERS, 1968, (50) : 5179 - &
  • [33] 1,1-DISUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES FROM ISOQUINOLINES
    NATSUME, M
    KIUCHI, K
    KUMADAKI, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1972, 20 (07) : 1592 - +
  • [34] Synthesis of 1,1-disubstituted tetrahydro-β-carbolines from 2-methyleneaziridines
    Mumford, Peter M.
    Shiers, Jason J.
    Tarver, Gary J.
    Hayes, Jerome F.
    Shipman, Michael
    TETRAHEDRON LETTERS, 2008, 49 (21) : 3489 - 3491
  • [35] 1,1-disubstituted tetrahydroisoquinolines from enaminones via Pictet-Spengler reaction
    Venkov, AP
    Angelov, PA
    SYNTHETIC COMMUNICATIONS, 2003, 33 (17) : 3025 - 3033
  • [36] NUCLEOPHILIC RING-OPENING ADDITIONS TO 1,1-DISUBSTITUTED CYCLOPROPANES
    STEWART, JM
    WESTBERG, HH
    JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (06): : 1951 - &
  • [37] CHIRAL FORMAMIDINES - ASYMMETRIC-SYNTHESIS OF 1,1-DISUBSTITUTED TETRAHYDROISOQUINOLINES
    MEYERS, AI
    GONZALEZ, MA
    STRUZKA, V
    AKAHANE, A
    GUILES, J
    WARMUS, JS
    TETRAHEDRON LETTERS, 1991, 32 (40) : 5501 - 5504
  • [38] Enantioselective Nickel-Catalyzed Hydrosilylation of 1,1-Disubstituted Allenes
    Liu, Tao
    Mao, Xin-Rui
    Song, Shuo
    Chen, Zi-Yang
    Wu, Yichen
    Xu, Li-Ping
    Wang, Peng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (11)
  • [39] Nickel-Catalyzed Enantioselective Hydrosilylation of 1,1-Disubstituted Allenes
    Chen Shaowei
    Shen Xiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (03) : 1213 - 1214
  • [40] CONVENIENT SYNTHESIS OF 1,1-DISUBSTITUTED 1,4-BUTANEDIOLS AND DERIVATIVES
    UMIO, S
    UEDA, I
    NOJIMA, H
    JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (08) : 855 - &