REACTIONS OF 3-SUBSTITUTED QUINOLINE 1-OXIDES WITH ACYLATING AGENTS

被引:16
作者
MIURA, Y
TAKAKU, S
NAWATA, Y
HAMANA, M
机构
[1] Exploratory Laboratories, Chugai Pharmaceutical Co., Ltd. 1-135 Komakado, Shizuoka Prefecture, 412, Gotenba
关键词
D O I
10.3987/COM-91-5788
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactions of 3-fluoro- (1a), 3-bromo,- (1b), 3-methyl- (1c), 3-methoxy- (1d) and 3-acetamidoquinoline 1-oxides (1e) with acylating agents (POCl3, Ac2O, TsCl and PhCOCl) were examined (Table). While only 2-substituted quinolines were obtained from 1a and 1b, fair amounts of 4-substituted products were formed in reactions of 1d, the sole formation of the 4-acetoxyquinoline (6) with Ac2O being the most significant result. 2-Chloroquinolines, 4-chloroquinolines and 2-tosyloxy-quinolines were formed (and sometimes predominate) in addition to 2-quinolinones in reactions with TsCl.
引用
收藏
页码:1579 / 1586
页数:8
相关论文
共 13 条
[1]  
Hamana M, 1966, Yakugaku Zasshi, V86, P1090
[2]  
HAMANA M, 1964, YAKUGAKU ZASSHI, V84, P34
[3]  
JONES G, 1982, CHEM HETEROCYCLIC CO, V32, P491
[4]   NITRATION OF 3-PHENYLQUINOLINE [J].
KASLOW, CE ;
BUCHNER, B .
JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (02) :271-276
[5]   HETARINE .6. UBER DAS INTERMEDIARE AUFTRETEN VON 3.4-DEHYDRO-CARBOSTYRIL UND 1-METHYL-3.4-DEHYDRO-CARBOSTYRIL [J].
KAUFFMANN, T ;
SCHULZ, J .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (06) :1837-+
[6]  
KOBAYASHI Y, 1969, CHEM PHARM BULL, V17, P2335
[7]   BENZYLIC HALOGENATION OF METHYLQUINOLINES [J].
LYLE, RE ;
BRISTOL, JA ;
KANE, MJ ;
PORTLOCK, DE .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (24) :3967-&
[8]   POLARIZATION OF AROMATIC HETEROCYCLIC COMPOUNDS .68. REACTION OF ACETIC ANHYDRIDE ON QUINOLINE-N-OXIDE [J].
OCHIAI, E ;
OKAMOTO, T .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1948, 68 (3-4) :88-90
[9]  
OCHIAI E, 1958, YAKUGAKU ZASSHI, V78, P584
[10]  
OCHIAI E, 1956, YAKUGAKU ZASSHI, V76, P1321