An improved synthesis of methyl 1,3-Dihydro-2H-pyrrolo[3,4-b]quinoline-2-carboxylate

被引:16
作者
Akue-Gedu, Rufine
Gautret, Philippe
Lelieur, Jean-Pierre
Rigo, Benoit
机构
[1] Ecole Hautes Etud Ingn, Grp Rech Inhibit Proliferat Cellulaire, EA 2692, F-59046 Lille, France
[2] Ecole Hautes Etud Ingn, CNRS, Lab Spectrochim Infrarouge & Raman, UMR 8516, F-59046 Lille, France
来源
SYNTHESIS-STUTTGART | 2007年 / 21卷 / 21期
关键词
heterocycles; quinolines; pyrrolidinones; Friedlander condensation; 1,3-dihydro-2H-pyrrolo[3,4-b]quinolines;
D O I
10.1055/s-2007-990821
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optimization of an old route leads very easily, in four steps, to methyl 1,3-dihydro-2H-pyrrolo[3,4-b]quinoline-2-carboxylate in 45% yield from commercial starting materials. This procedure can be compared to recently described methods whose yields were only 23-28% and required five to seven steps from advanced intermediates and chromatographic purifications. Moreover, using this method, the title compound can now be obtained in large quantities.
引用
收藏
页码:3319 / 3322
页数:4
相关论文
共 43 条
[1]   SYNTHESIS OF 4-(2-CHLOROETHYL)-2,3-DIHYDRO[1,4]OXAZINO[2,3-B]QUINOLINE AND 4-(2-CHLOROETHYL)-2,3-DIHYDROPYRIDO[2,3-B][1,4]OXAZINE [J].
ANDERSON, WK ;
DALVIE, DK .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (06) :1533-1536
[2]   2-Aminobenzaldehydes from quinolinium salts and alkaline hydrogen peroxide [J].
Apple, IA ;
Meth-Cohn, O .
ARKIVOC, 2002, :4-14
[3]   CINNOLINES .3. SYNTHESIS OF BZ-SUBSTITUTED 3-NITROCINNOLINES AND 3-AMINOCINNOLINES [J].
BAUMGARTEN, HE ;
PEDERSEN, DL ;
HUNT, MW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (08) :1977-1981
[4]   On tricyclic lactones from chinaldine carbonic acid-(3)-ester and on [3-carboxy-chinolyl-(2)]-pyrunic acid diethyl ester [J].
Borsche, W ;
Doeller, W ;
Wagner-Roemmich, M .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1943, 76 :1099-1104
[5]   Towards new camptothecins.: Part 3:: Synthesis of 5-methoxycarbonyl camptothecin [J].
Brunin, T ;
Legentil, L ;
Hénichart, JP ;
Rigo, B .
TETRAHEDRON, 2006, 62 (17) :3959-3968
[6]   Towards new camptothecins.: Part 2:: Synthesis of the ABCD ring scaffold substituted by a carboxyl group in the 5-position [J].
Brunin, T ;
Hénichart, JP ;
Rigo, B .
TETRAHEDRON, 2005, 61 (33) :7916-7923
[7]   STUDIES ON PYRROLIDONES - CONVENIENT SYNTHESES OF METHYL, METHYL N-METHYLPYROGLUTAMATE AND METHYL N-METHOXYMETHYLPYROGLUTAMATE [J].
CAULIEZ, P ;
RIGO, B ;
FASSEUR, D ;
COUTURIER, D .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (04) :1143-1146
[8]   Facile syntheses of ABC ring skeleton of camptothecin and related alkaloids [J].
Chavan, SP ;
Pasupathy, K ;
Sivappa, R ;
Venkatraman, MS .
SYNTHETIC COMMUNICATIONS, 2004, 34 (17) :3099-3110
[9]  
CHENG CC, 1982, ORG REACTIONS, V28, P37
[10]   A preparation of m-dimethylaminobenzaldehyde Part II [J].
Cocker, W ;
Harris, JO ;
Loach, JV .
JOURNAL OF THE CHEMICAL SOCIETY, 1938, :751-753