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
[11]   SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES [J].
DREWES, SE ;
ROOS, GHP .
TETRAHEDRON, 1988, 44 (15) :4653-4670
[12]   Application of Baylis-Hillman methodology in a novel synthesis of quinoline derivatives [J].
Familoni, OB ;
Kaye, PT ;
Klaas, PJ .
CHEMICAL COMMUNICATIONS, 1998, (23) :2563-2564
[13]   Synthesis of methyl (E)-2-nitromethylcinnamates derived from Baylis-Hillman acetates and conversion into several coumarin derivatives [J].
Hong, WP ;
Lee, KJ .
SYNTHESIS-STUTTGART, 2005, Georg Thieme Verlag (01) :33-38
[14]   Synthesis of 3-nitro-1H-indole-2-carboxylic acid ethyl ester derivatives from Baylis-Hillman adducts [J].
Horn, CR ;
Perez, M .
SYNLETT, 2005, (09) :1480-1482
[15]  
Huisgen R., 1963, ANGEW CHEM INT EDIT, V2, P633, DOI [10.1002/anie.196306331, DOI 10.1002/ANIE.196306331, DOI 10.1002/ANIE.19630633]
[16]  
Huisgen R., 1963, Angew. Chem. Int. Ed, V2, P565, DOI DOI 10.1002/ANIE.196305651
[17]   SYNTHETIC REACTIONS USING ISOXAZOLE COMPOUNDS [J].
KASHIMA, C .
HETEROCYCLES, 1979, 12 (10) :1343-1368
[18]   REACTION OF SPIRONAPHTHALENONES WITH HYDROXYLAMINE HYDROCHLORIDE .4. [J].
KASTURI, TR ;
SATTIGERI, JA ;
PRAGNACHARYULU, PVP ;
CAMEROON, TS ;
PRADEEP, B .
TETRAHEDRON, 1995, 51 (10) :3051-3060
[19]  
Kaye PT, 2001, SYNTHESIS-STUTTGART, P2389
[20]  
Kaye PT, 2003, SYNTHESIS-STUTTGART, P531