New syntheses of 5,6-and 7,8-diaminoquinolines

被引:6
作者
Bella, Maros [1 ]
Milata, Viktor [2 ]
机构
[1] Slovak Acad Sci, Inst Chem, SK-84538 Bratislava, Slovakia
[2] Slovak Univ Technol Bratislava, Fac Chem & Food Technol, Dept Organ Chem, SK-81237 Bratislava, Slovakia
关键词
chlorination; deselenation; nitrogen heterocycles; o-diaminoquinolines; selenadiazoloquinolones; DERIVATIVES;
D O I
10.3762/bjoc.9.302
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 5,6- and 7,8-diaminoquinoline derivatives starting from angularly annelated selenadiazoloquinolones is presented. Simple chlorination of the pyridone ring followed by reductive deselenation of the 1,2,5-selenadiazole ring afforded novel 4-chloro-o-diaminoquinolines. Dechlorination of 4-chloro-7,8-diaminoquinoline gave 7,8-diaminoquinoline hydrochloride which was successfully employed as starting material in the synthesis of condensed nitrogen heterocycles.
引用
收藏
页码:2669 / 2674
页数:6
相关论文
共 19 条
[1]   2-(2-Furyl)-1(3)H-imidazo[4,5-f]quinoline. Synthesis and Electrophilic Substitution Reactions [J].
Aleksandrov, A. A. ;
Dedeneva, A. S. ;
Vlasova, E. V. ;
El'chaninov, M. M. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (01) :120-123
[2]   Synthesis of [1,2,5]selenadiazolo[3,4-f]quinolone derivatives by the Gould-Jacobs reaction of 5-amino-2,1,3-benzoselenadiazole [J].
Bella, Maros ;
Schultz, Marcel ;
Milata, Viktor .
ARKIVOC, 2012, :242-251
[3]   Application of the Gould-Jacobs reaction to 4-amino-2,1,3-benzoselenadiazole [J].
Bella, Maros ;
Schultz, Marcel ;
Milata, Viktor ;
Konarikova, Katarina ;
Breza, Martin .
TETRAHEDRON, 2010, 66 (41) :8169-8174
[4]   REACTION OF ACETOIN AND HYDROXYACETALDEHYDE WITH CYCLOHEXYLAMINE [J].
CARSON, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (17) :4337-4338
[5]   SUBSTITUTED 1,10-PHENANTHROLINES .11. AZA DERIVATIVES [J].
CASE, FH ;
BRENNAN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (23) :6297-6301
[6]  
Colonna M., 1951, GAZZ CHIM ITAL, V81, P744
[7]   SYNTHESIS OF MUTAGENIC METHYL-SUBSTITUTED AND PHENYL-SUBSTITUTED 2-AMINO-3H-IMIDAZO[4,5-F]QUINOXALINES VIA 2,1,3-BENZOSELENADIAZOLES [J].
GRIVAS, S ;
TIAN, W ;
RONNE, E ;
LINDSTROM, S ;
OLSSON, K .
ACTA CHEMICA SCANDINAVICA, 1993, 47 (05) :521-528
[8]  
Hudson A, 2005, NAME REACTIONS HETER, P488
[9]  
HUISGEN R, 1948, LIEBIGS ANN CHEM, V559, P101, DOI DOI 10.1002/JLAC.19485590204
[10]  
Lee JH, 2006, HETEROCYCLES, V70, P571