The dipolar route to naphtho[2,1-c]isoxazoles from the Baylis-Hillman adducts of 2-alkynylbenzaldehydes

被引:23
作者
Ji, Sang-Hoon [1 ]
Hong, Wan Pyo [1 ]
Ko, Seung Ho [1 ]
Lee, Kee-Jung [1 ]
机构
[1] Hanyang Univ, Dept Chem Engn, Organ Synth Lab, Seoul 133791, South Korea
关键词
D O I
10.1002/jhet.5570430344
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new synthesis of 4-carbomethoxynaphtho[2,1-c]isoxazoles 4a-d from methyl 3-(alkynylphenyl)-2-nitromethyl-2-propenoates 2a-d by the intramolecular nitrile oxide cycloaddition is described. The latter are readily obtained from 2-alkynylbenzaldehydes through the Baylis-Hillman adduct acetates 1a-d followed by nucleophilic substitution of nitrite anion.
引用
收藏
页码:799 / 801
页数:3
相关论文
共 40 条
[21]   Application of Baylis-Hillman methodology in a chemoselective synthesis of 3-acyl-2H-1-chromenes [J].
Kaye, PT ;
Nocanda, XW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (09) :1331-1332
[22]   Synthesis of 3-ethoxycarbonyl-4-hydroxyquinoline N-oxides from the Baylis-Hillman adducts of o-nitrobenzaldehydes [J].
Kim, JN ;
Lee, KY ;
Kim, HS ;
Kim, TY .
ORGANIC LETTERS, 2000, 2 (03) :343-345
[23]   Synthesis of 3-quinolinecarboxylic acid esters from the Baylis-Hillman adducts of 2-halobenzaldehyde N-tosylimines [J].
Kim, JN ;
Lee, HJ ;
Lee, KY ;
Kim, HS .
TETRAHEDRON LETTERS, 2001, 42 (22) :3737-3740
[24]   Synthesis of cyclic compounds from the Baylis-Hillman adducts [J].
Kim, JN ;
Lee, KY .
CURRENT ORGANIC CHEMISTRY, 2002, 6 (07) :627-645
[25]   Synthesis of N-substituted 1,4-dihydroquinolines from the Baylis-Hillman acetates via the successive SN2′-SNAr isomerization strategy [J].
Kim, JN ;
Kim, HS ;
Gong, JH ;
Chung, YM .
TETRAHEDRON LETTERS, 2001, 42 (47) :8341-8344
[26]   Synthesis of 5H-1,2,3-triazolo[4,3-a][2]benzazepines from the Baylis-Hillman adducts of 2-alkynylbenzaldehydes [J].
Ko, SH ;
Lee, KJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 41 (04) :613-616
[27]   RECENT DEVELOPMENTS IN ISOXAZOLE CHEMISTRY [J].
KOCHETKOV, NK ;
SOKOLOV, SD .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1963, 2 :365-422
[29]   Synthesis of 4H-tetrazolo[1,5-a][1]benzazepines from the Baylis-Hillman adducts of 2-azidobenzaldehyde [J].
Lee, CH ;
Song, YS ;
Cho, HI ;
Yang, JW ;
Lee, KJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (06) :1103-1106
[30]   SYNTHESIS OF COMPOUNDS RELATED TO MUSCIMOL (PANTHERINE, AGARIN) [J].
LOEV, B ;
WILSON, JW ;
GOODMAN, MM .
JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (04) :738-+