ORGANIC AZIDES IN HETEROCYCLIC SYNTHESIS .15. NUCLEOPHILIC-SUBSTITUTION AND RING-CLOSURE REACTIONS OF 4-CHLORO-3-NITRO-2-QUINOLONES

被引：65
作者：
ROSCHGER, P
FIALA, W
STADLBAUER, W
机构：
[1] Institute of Organic Chemistry, Karl Franzens University of Graz, Graz, A-8010
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1992年 / 29卷 / 01期
关键词：
D O I：
10.1002/jhet.5570290141
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
4-Chloro-3-nitro-2-quinolones 3 obtained from the 4-hydroxy quinolones 1 by nitration and chlorination, reacted with sodium azide to the 4-azido derivatives 4 which cyclized on thermolysis to yield the furoxanes 5. Nucleophilic substitution reactions of 3 led to the 4-amino-, 4-fluoro- and 4-alkoxy-3-nitroquinolones 7, 8 and 9, respectively. With thiols either 4-thio-3-nitro- 10 or 3,4-dithioquinolones 11 were obtained depending on the basic catalyst.
引用
收藏
页码：225 / 231
页数：7
相关论文
共 35 条
[1]   CHEMICAL CONSTITUENTS OF AUSTRALIAN FLINDERSIA SPECIES .17. STRUCTURE OF IFFLAIAMINE [J].
BOSSON, JA ;
ROBERTSON, AV ;
RASMUSSE.M ;
RITCHIE, E ;
TAYLOR, WC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1963, 16 (03) :480-&
[2]   HETEROCYCLIC REARRANGEMENTS .4. FUROXANO- AND FURAZANO-BENZOFUROXAN [J].
BOULTON, AJ ;
GRAY, ACG ;
KATRITZKY, AR .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (NOV) :5958-+
[3]   THE REACTION BETWEEN DIPHENYLAMINE AND MALONIC ESTERS [J].
BOWMAN, RE ;
CAMPBELL, A ;
TANNER, EM .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (JAN) :444-447
[4]   4-HYDROXY-3-NITRO-2-QUINOLONES AND RELATED COMPOUNDS AS INHIBITORS OF ALLERGIC REACTIONS [J].
BUCKLE, DR ;
CANTELLO, BCC ;
SMITH, H ;
SPICER, BA .
JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (07) :726-732
[5]   2H-BENZIMIDAZOLES .5. CONVENIENT SYNTHONS FOR TRICYCLIC HETEROCYCLES [J].
CADA, A ;
KRAMER, W ;
NEIDLEIN, R ;
SUSCHITZKY, H .
HELVETICA CHIMICA ACTA, 1990, 73 (04) :902-911
[6]  
DEEB A, 1991, LIEBIGS ANN CHEM, P1225
[7]   PYROLYSIS OF ARYL AZIDES .6. IDENTIFICATION OF NEIGHBORING GROUP EFFECTS IN PYROLYSIS OF AZIDOPYRIDINES AND AZIDOQUINOLINES [J].
DYALL, LK ;
WAH, WM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (07) :1045-1059
[8]   NON-STEROIDAL ANTIINFLAMMATORY AGENTS .2. SYNTHESIS OF 4-HYDROXY-1-METHYL-2-OXO-DIHYDROQUINOLIN-3-YL ACETIC-ACID AND RELATED TETRAZOLYL DERIVATIVES [J].
FABER, K ;
KAPPE, T .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (06) :1881-1883
[9]   60 YEARS OF STAUDINGER REACTION [J].
GOLOLOBOV, YG ;
ZHMUROVA, IN ;
KASUKHIN, LF .
TETRAHEDRON, 1981, 37 (03) :437-472
[10]   N-OXIDES AND RELATED COMPOUNDS .19. PROTON RESONANCE SPECTRA AND STRUCTURE OF BENZOFUROXAN AND ITS NITRO-DERIVATIVES [J].
HARRIS, RK ;
BAILEY, AS ;
PATERSON, WG ;
OKSNE, S ;
KATRITZKY, AR .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (JAN) :197-&
1234