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 18 条
[1]  
CROCE PD, 1985, J CHEM SOC P1, P2621
[2]   REVERSAL OF REGIOCHEMISTRY IN THE SYNTHESIS OF ISOXAZOLES BY NITRILE OXIDE CYCLOADDITIONS [J].
EASTON, CJ ;
HUGHES, CM ;
TIEKINK, ERT ;
LUBIN, CE ;
SAVAGE, GP ;
SIMPSON, GW .
TETRAHEDRON LETTERS, 1994, 35 (21) :3589-3592
[3]   Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp® [J].
Easton, CJ ;
Heath, GA ;
Hughes, CMM ;
Lee, CKY ;
Savage, GP ;
Simpson, GW ;
Tiekink, ERT ;
Vuckovic, GJ ;
Webster, RD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (10) :1168-1174
[4]  
Hamme AT, 2005, HETEROCYCLES, V65, P2885
[5]   FRONTIER MOLECULAR-ORBITALS OF 1,3 DIPOLES AND DIPOLAROPHILES [J].
HOUK, KN ;
SIMS, J ;
DUKE, RE ;
STROZIER, RW ;
GEORGE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7287-7301
[6]   ORIGIN OF REACTIVITY, REGIOSELECTIVITY, AND PERISELECTIVITY IN 1,3-DIPOLAR CYCLOADDITIONS [J].
HOUK, KN ;
SIMS, J ;
WATTS, CR ;
LUSKUS, LJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7301-7315
[7]   FRONTIER MOLECULAR-ORBITAL THEORY OF CYCLOADDITION REACTIONS [J].
HOUK, KN .
ACCOUNTS OF CHEMICAL RESEARCH, 1975, 8 (11) :361-369
[8]  
JIMENEZ R, 1993, HETEROCYCLES, V35, P591
[9]   Isoxazole-type derivatives related to combretastatin A-4, synthesis and biological evaluation [J].
Kaffy, Julia ;
Pontikis, Renee ;
Carrez, Daniele ;
Croisy, Alain ;
Monneret, Claude ;
Florent, Jean-Claude .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (12) :4067-4077
[10]   Heterocyclic nucleoside analogues: Design and synthesis of antiviral, modified nucleosides containing isoxazole heterocycles [J].
Lee, YS ;
Kim, BH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (10) :1395-1397