A convenient synthesis of pyrrolo[3,4-c]quinolines

被引：15
|
作者：
Virányi, A
Nyerges, M
Blaskó, G
Töke, L
机构：
[1] Tech Univ Budapest, Dept Organ Chem Technol, Hungarian Acad Sci, Res Grp, H-1521 Budapest, Hungary
[2] Egis Pharmaceut, H-1475 Budapest, Hungary
来源：
SYNTHESIS-STUTTGART | 2003年 / 17期
关键词：
amino acids; cyclizations; cycloaddition; lactams; quinolines;
D O I：
10.1055/s-2003-42425
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new route to the pyrrolo[3,4-c]quinoline ring system has been developed. The synthesis proceeds stereoselectively in three steps, using 1,3-dipolar cycloaddition of azomethine ylides as a key step. First, a series of 4-arylpyrrolidine-3-carboxylic acids have been prepared from the appropriate cinnamic esters and a non-stabilized azomethine ylide. The reduction of a nitro group on the aromatic ring was followed by acid-catalyzed intramolecular lactam formation.
引用
收藏
页码：2655 / 2660
页数：6
相关论文
共 50 条
  • [21] Synthesis and properties of benzo[c]-, pyrrolo[3,4-c]-, and thieno[3,4-c]-pyrrole-4,6-dione copolymers
    Lu, Yong
    Lei, Yanlian
    Wu, Bo
    Xu, Xiaofeng
    Zhu, Furong
    Hu, Xiao
    Ong, Beng S.
    Ng, Siu Choon
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (04) : 2642 - 2650
  • [22] A NOVEL SYNTHESIS OF 1,3,4-TRIMETHYLFURO[3,4-C]QUINOLINES
    NIWAS, S
    KUMAR, S
    BHADURI, AP
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1983, 22 (08): : 725 - 726
  • [23] Convenient synthesis of functionalized pyrrolo[3,4-b]pyridines and pyrrolo[3,4-b]quinolines via three-component reactions
    Jiang, Yan-Hong
    Xiao, Man
    Yan, Chao-Guo
    RSC ADVANCES, 2016, 6 (42) : 35609 - 35616
  • [24] CYCLIZATION OF PHENYLHYDRAZONES OF SUBSTITUTED PYRROL-3-ALDEHYDES TO 2H-PYRROLO[3,4-C]-QUINOLINES
    FRITZ, H
    SCHENK, S
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1972, 762 (AUG): : 121 - &
  • [25] Pyridazino[3,4-c]quinolines and pyridazino[4,5-c]quinolines -: synthesis and investigation of lipoxygenase inhibition
    Görlitzer, K
    Fabian, J
    Jones, PG
    Frohberg, P
    Drutkowski, G
    PHARMAZIE, 2002, 57 (06): : 362 - 371
  • [26] NICETHAMIDE ANALOGS .7. SYNTHESIS OF A PYRROLO [3,4-B]- AND PYRROLO [3,4-C]PYRIDINONE AS NICETHAMIDE ANALOGS
    SATTLER, HJ
    SCHUNACK, W
    CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (04): : 1003 - 1009
  • [27] Furo[2,3-c]quinolines and furo[3,4-c]quinolines -: synthesis and investigation of lipoxygenase inhibition
    Görlitzer, K
    Fabian, J
    Jones, PG
    Frohberg, P
    Drutkowski, G
    PHARMAZIE, 2002, 57 (03): : 159 - 168
  • [28] CONDENSED HETEROCYCLES .13. SYNTHESIS OF "[1,2,5]THIADIAZOLO[3,4-C]QUINOLINES AND [1,2,5]SELENADIAZOLO[3,4-C]QUINOLINES
    SHARMA, KS
    SINGH, RP
    KUMARI, S
    SYNTHESIS-STUTTGART, 1983, (07): : 581 - 581
  • [29] Domino Reaction for Synthesis of Spiro[pyrazole-4,5′-pyrrolo[3,4-c]carbazoles] and Spiro[pyrrolo[3,4-c]carbazole-5,5′-thiazoles]
    Yan, Chen
    Sun, Jing
    Han, Ying
    Yan, Chao-Guo
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (10) : 2632 - 2637
  • [30] SYNTHESIS OF PYRROLO[3,4-C]PYRAZOLE DERIVATIVES BY INTRAMOLECULAR CYCLOADDITION OF NITRILE IMINES
    GARANTI, L
    SALA, A
    ZECCHI, G
    SYNTHETIC COMMUNICATIONS, 1976, 6 (04) : 269 - 275
12345