An efficient large scale synthesis of coumarins by a dealkylative boron-mediated ring closure of 3-(orthomethoxyaryl)propenoic esters.

被引:19
作者
Dubuffet, T [1 ]
Loutz, A [1 ]
Lavielle, G [1 ]
机构
[1] Inst Rech Servier, F-78290 Croissy Sur Seine, France
关键词
D O I
10.1080/00397919908086054
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various substituted coumarins 3 were prepared via a dealkylative boron-mediated ring closure of ortho-methoxycinnamates 2.
引用
收藏
页码:929 / 936
页数:8
相关论文
共 22 条
[11]  
EFFENBERGER F, 1969, LIEBIGS ANN CHEM, V729, P246
[12]   CLEAVAGE OF PROTECTING GROUPS WITH BORON TRIBROMIDE [J].
FELIX, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (10) :1427-1429
[13]  
Feuer G, 1974, Prog Med Chem, V10, P85, DOI 10.1016/S0079-6468(08)70267-4
[14]   SYNTHESIS OF ANGULAR DIOXINOCOUMARINS [J].
GUILLAUMET, G ;
HRETANI, M ;
COUDERT, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (01) :193-197
[15]   A CONVENIENT SYNTHESIS OF A SIMPLE COUMARIN FROM SALICYLALDEHYDE AND WITTIG REAGENT .1. A SYNTHESIS OF METHOXYCOUMARIN AND HYDROXYCOUMARIN [J].
HARAYAMA, T ;
KATSUNO, K ;
NISHIOKA, H ;
FUJII, M ;
NISHITA, Y ;
ISHII, H ;
KANEKO, Y .
HETEROCYCLES, 1994, 39 (02) :613-622
[16]   CONVENIENT SYNTHESIS OF A SIMPLE COUMARIN FROM SALICYLALDEHYDE AND WITTIG REAGENT .3. SYNTHESIS OF NITROCOUMARINS [J].
HARAYAMA, T ;
NAKATSUKA, K ;
NISHIOKA, H ;
MURAKAMI, K ;
OHMORI, Y ;
TAKEUCHI, Y ;
ISHII, H ;
KENMOTSU, K .
HETEROCYCLES, 1994, 38 (12) :2729-2738
[17]   C-13 NMR-SPECTROSCOPY OF HETEROCYCLIC-COMPOUNDS .7. CHARACTERIZATION OF 7-FLUOROCOUMARIN FROM A 20-MHZ STUDY OF CHEMICAL-SHIFTS, CARBON-PROTON AND CARBON-FLUORINE COUPLING-CONSTANTS [J].
HUCKERBY, TN .
JOURNAL OF MOLECULAR STRUCTURE, 1979, 54 (JUL) :289-292
[18]   SYNTHETIC APPLICATION OF LITHIATION REACTIONS .7. NEW SYNTHESES OF LINEAR AND ANGULAR NAPHTHOFURANS AND BENZOCOUMARINS [J].
NARASIMHAN, NS ;
MALI, RS .
TETRAHEDRON, 1975, 31 (08) :1005-1009
[19]  
NARASIMHAN NS, 1979, SYNTHESIS-STUTTGART, P906
[20]  
SATO K, 1987, J CHEM SOC P1, V8, P1753