Competitive intramolecular nucleophilic aromatic substitution: A new route to coumarins

被引:5
作者
Alonso, C [1 ]
Olmstead, MM [1 ]
Nantz, MH [1 ]
Kurth, MJ [1 ]
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
关键词
D O I
10.1039/b009172n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
4-Hydroxy-3-(2'-pyridyl)coumarins (4) (R=6-Cl, H, 6-NO2, 8-NO2) were prepared in moderate to good yields by the intramolecular nucleophilic aromatic substitution reaction of beta -ketoesters (I) in refluxing xylenes; evidence for the reversible formation of benzo[c]quinolizinium III from I (X = 4 -Cl), with eventual formation of 4 (R = 6-Cl), is also presented.
引用
收藏
页码:639 / 640
页数:2
相关论文
共 10 条
[1]   Development of substituted benzo[c]quinolizinium compounds as novel activators of the cystic fibrosis chloride channel [J].
Becq, F ;
Mettey, Y ;
Gray, MA ;
Galietta, LJV ;
Dormer, RL ;
Merten, M ;
Métayé, T ;
Chappe, V ;
Marvingt-Mounir, C ;
Zegarra-Moran, O ;
Tarran, R ;
Bulteau, L ;
Dérand, R ;
Pereira, MMC ;
McPherson, MK ;
Rogier, C ;
Joffre, M ;
Argent, BE ;
Sarrouilhe, D ;
Kammouni, W ;
Figarella, C ;
Verrier, B ;
Gola, M ;
Vierfond, JM .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (39) :27415-27425
[2]  
BHAWAL BM, 1991, SYNTHESIS-STUTTGART, P113
[3]   The solid-phase Zincke reaction:: Preparation of ω-hydroxy pyridinium salts in the search for CFTR activation [J].
Eda, M ;
Kurth, MJ ;
Nantz, MH .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5131-5135
[4]   BENZO(C)QUINOLIZINIUM SALTS VIA INTRAMOLECULAR CYLIZATION [J].
FOZARD, A ;
BRADSHER, CK .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) :2346-&
[5]   A BACTERIAL SYSTEM FOR INVESTIGATING TRANSPORT EFFECTS OF CYSTIC-FIBROSIS ASSOCIATED MUTATIONS [J].
GIBSON, AL ;
WAGNER, LM ;
COLLINS, FS ;
OXENDER, DL .
SCIENCE, 1991, 254 (5028) :109-111
[6]   One-step synthesis of new heterocyclic azacyanines [J].
Haddadin, MJ ;
Kurth, JM ;
Olmstead, MM .
TETRAHEDRON LETTERS, 2000, 41 (30) :5613-5616
[7]   IDENTIFICATION OF THE CYSTIC-FIBROSIS GENE - GENETIC-ANALYSIS [J].
KEREM, BS ;
ROMMENS, JM ;
BUCHANAN, JA ;
MARKIEWICZ, D ;
COX, TK ;
CHAKRAVARTI, A ;
BUCHWALD, M ;
TSUI, LC .
SCIENCE, 1989, 245 (4922) :1073-1080
[8]   REGULATION OF CHLORIDE CHANNELS BY PROTEIN KINASE-C IN NORMAL AND CYSTIC-FIBROSIS AIRWAY EPITHELIA [J].
LI, M ;
MCCANN, JD ;
ANDERSON, MP ;
CLANCY, JP ;
LIEDTKE, CM ;
NAIRN, AC ;
GREENGARD, P ;
WELSH, MJ .
SCIENCE, 1989, 244 (4910) :1353-1356
[9]  
RIORDAN JR, 1989, SCIENCE, V245, P1066
[10]   IDENTIFICATION OF THE CYSTIC-FIBROSIS GENE - CHROMOSOME WALKING AND JUMPING [J].
ROMMENS, JM ;
IANNUZZI, MC ;
KEREM, BS ;
DRUMM, ML ;
MELMER, G ;
DEAN, M ;
ROZMAHEL, R ;
COLE, JL ;
KENNEDY, D ;
HIDAKA, N ;
ZSIGA, M ;
BUCHWALD, M ;
RIORDAN, JR ;
TSUI, LC ;
COLLINS, FS .
SCIENCE, 1989, 245 (4922) :1059-1065