SYNTHESIS OF 11H-PYRIDO[2,3-A]CARBAZOLES AND 6H-PYRIDO[3,2-B]CARBAZOLES FROM 8-METHOXY BROMOQUINOLINES

被引:10
|
作者
TRECOURT, F [1 ]
MALLET, M [1 ]
MONGIN, F [1 ]
QUEGUINER, G [1 ]
机构
[1] INST NATL SCI APPL ROUEN,IRCOF,CHIM ORGAN FINE & HETEROCYCL LAB,CNRS,URA 1429,F-76131 MONT ST AIGNAN,FRANCE
关键词
D O I
10.1016/0040-4020(95)00726-O
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cross-coupling reaction via substituted 7-bromoquinolines 1, 8 and (2-aminophenyl)boric acids afforded substituted 7-(2-aminophenyl)quinolines 3a-b, 10 from which synthesis of either 11H-pyrido[2,3-a]carbazoles 4a-b, 11 via C-8 cyclization or 6H-pyrido[3,2-b]carbazoles 6a-b, 13 via C-6 cyclization could be achieved.
引用
收藏
页码:11743 / 11750
页数:8
相关论文
共 50 条
  • [31] CHEMISTRY OF H-6-PYRIDO[4,3-B]CARBAZOLES .5. SIMPLE SYNTHESIS OF ELLIPTICINES
    SAINSBURY, M
    SCHINAZI, RF
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (10): : 1155 - 1160
  • [32] NEW SYNTHESIS OF THE 6H-PYRIDO[4,3-B]CARBAZOLES ELLIPTICINE AND OLIVACINE VIA CYCLOADDITION OF 2-PHENYLSULFONYL 1,3-DIENES TO INDOLES
    BACKVALL, JE
    PLOBECK, NA
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15): : 4528 - 4531
  • [33] SYNTHESIS OF 5H-PYRIDO[2,3-A]PHENOXAZIN-5-ONE AND 5H-PYRIDO[3,2-A]PHENOXAZIN-5-ONE DERIVATIVES
    NANYA, S
    MAEKAWA, E
    HAYAKAWA, H
    KITAGUCHI, Y
    UENO, Y
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (06) : 1483 - 1485
  • [34] Metal-Free [3+2] Tandem Cyclization Synthesis of Unique 11H-Pyrido[3,2:4,5]Pyrrolo[3,2-b]Indolizine from 7-Azaindoles and Pyridotriazoles
    Zhang, Guo-Tai
    Zhang, Jing
    Xu, Yan-Jun
    Dong, Lin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4197 - 4201
  • [35] Synthesis of novel pyrido[3′,2′:5,6]thiopyrano[3,2-b]indol-5(6H)-ones and 6H-pyrido[3′,2′:5,6]thiopyrano[4,3-b]quinolines, two new heterocyclic ring systems
    Da Settimo, A
    Marini, AM
    Primofiore, G
    Da Settimo, F
    Salerno, S
    Simorini, F
    Pardi, G
    La Motta, C
    Bertini, D
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (05) : 1001 - 1006
  • [36] UNEXPECTED FORMATION OF A 11H-PYRIDO[2,1-B]QUINAZOLIN-11-ONE DERIVATIVE FROM 5,11-DIHYDRO-6H-PYRIDO[2,3-B]-1,4-BENZODIAZEPIN-6-ONE
    BUDESINSKY, M
    SYMERSKY, J
    PODLAHA, J
    PODLAHOVA, J
    POLIVKA, Z
    PROTIVA, M
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (05) : 1229 - 1235
  • [37] Synthesis of novel 5H,11H-pyrido[2′,3′:2,3]thiopyrano[4,3-b]-indoles by Fischer-indole cyclization
    Da Settimo, A
    Marini, AM
    Primofiore, G
    Da Settimo, F
    Salerno, S
    La Motta, C
    Pardi, G
    Ferrarini, PL
    Mori, C
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (02) : 379 - 382
  • [38] CHEMISTRY OF 6H-PYRIDO[4,3-B]CARBAZOLES .13. SYNTHESES OF RING-A-SUBSTITUTED AND RING-D-SUBSTITUTED ELLIPTICINES
    SAINSBURY, M
    SMITH, AD
    VONG, KK
    SCOPES, DIC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (11): : 2945 - 2954
  • [39] 8-Methyl-6-(4-methylpiperazin-1-yl)-11H-pyrido[2,3-b][1,4]benzodiazepine
    Spirlet, MR
    Graulich, A
    Liégeois, JF
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2003, 59 : O1990 - O1991
  • [40] SYNTHESIS OF 7H-PYRIDO[2,3-C]CARBAZOLES FROM 5-BROMO-8-METHOXYQUINOLINES VIA COUPLING AND AZIDE CYCLIZATION REACTIONS
    TRECOURT, F
    MONGIN, F
    MALLET, M
    QUEGUINER, G
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (04) : 1261 - 1267