N- vs O-alkylation in 2(1H)-quinolinone derivatives

被引:24
作者
Guo, ZX
Cammidge, AN [1 ]
McKillop, A
Horwell, DC
机构
[1] Univ E Anglia, Sch Chem Sci, Norwich NR4 7TJ, Norfolk, England
[2] Parke Davis Neurosci Res Ctr, Cambridge CB2 2QB, England
关键词
alkylation; quinolinones; phase transfer;
D O I
10.1016/S0040-4039(99)01422-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N- vs O-alkylation reactions of 8-benzyloxy-2(1H)-quinolinone have been investigated using both classical and phase transfer conditions. The influence of reaction solvents/conditions was found to have a dramatic effect on selectivity, with opposite trends to that observed for 2-pyridone alkylation. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6999 / 7002
页数:4
相关论文
共 8 条
[1]   N-ALKYLATION VS O-ALKYLATION IN THE MITSUNOBU REACTION OF 2-PYRIDONE [J].
COMINS, DL ;
GAO, JH .
TETRAHEDRON LETTERS, 1994, 35 (18) :2819-2822
[2]   SYNTHESIS AND ALDOSE REDUCTASE INHIBITORY ACTIVITY OF SUBSTITUTED 2-OXOQUINOLINE-1-ACETIC ACID-DERIVATIVES [J].
DERUITER, J ;
BRUBAKER, AN ;
WHITMER, WL ;
STEIN, JL .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (10) :2024-2028
[3]   ALKYLATION OF AMBIDENT ANIONS IN PHASE TRANSFER CATALYSIS - EXAMPLE OF HYDROXYPYRIDINES [J].
DOU, HJM ;
HASSANALY, P ;
METZGER, J .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (02) :321-323
[4]   NOVEL POSITIVE INOTROPIC AGENTS - SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF 6-(3-AMINO-2-HYDROXYPROPOXY)-2(1H)-QUINOLINONE DERIVATIVES [J].
FUJIOKA, T ;
TERAMOTO, S ;
MORI, T ;
HOSOKAWA, T ;
SUMIDA, T ;
TOMINAGA, M ;
YABUUCHI, Y .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (20) :3607-3612
[5]   APPLICATIONS OF PHASE-TRANSFER CATALYSIS IN HETEROCYCLIC CHEMISTRY [J].
GALLO, RJ ;
MAKOSZA, M ;
DOU, HJM ;
HASSANALY, P .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1984, 36 :175-234
[6]   ALKYLATIONS OF HETEROCYCLIC AMBIDENT ANIONS .2. ALKYLATION OF 2-PYRIDONE SALTS [J].
HOPKINS, GC ;
JONAK, JP ;
MINNEMEY.HJ ;
TIECKELM.H .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (12) :4040-&
[7]   Synthesis of a non-peptide analogue of omega-conotoxin MVIIA [J].
Menzler, S ;
Bikker, JA ;
Horwell, DC .
TETRAHEDRON LETTERS, 1998, 39 (41) :7619-7622
[8]  
NISHI T, 1983, CHEM PHARM BULL, V31, P852