Direct Synthesis of Pyrrolo[3,4-c]quinolines from the Domino Reaction of Tosylmethyl Isocyanides and Aminochalcones

被引:22
|
作者
Hu, Zhongyan [1 ]
Li, Yifei [1 ]
Pan, Ling [1 ]
Xu, Xianxiu [1 ]
机构
[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China
关键词
bicyclization; chalcones; domino reactions; pyrrolo[3,4-c]quinolones; tosylmethyl isocyanide; ALPHA-METALATED ISOCYANIDES; POTENT CASPASE-3 INHIBITORS; ARYL RADICAL CYCLIZATION; OLIGOSUBSTITUTED PYRROLES; ORGANIC-SYNTHESIS; CYCLOADDITION; EFFICIENT; PYRROLIZIDINES; NITROOLEFINS; HETEROCYCLES;
D O I
10.1002/adsc.201400468
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A tandem formal [3+2] cycloaddition/cyclization reaction of aminochalcones with tosylmethyl isocyanide derivatives was developed for the practical and convenient synthesis of diverse tricyclic pyrrolo[3,4-c]quinolines in high to excellent yields. In this domino process, three new bonds and two rings are successively formed at ambient conditions.
引用
收藏
页码:2974 / 2978
页数:5
相关论文
共 50 条
  • [1] One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)
    Lu, Xin-Mou
    Li, Jian
    Cai, Zhong-Jian
    Wang, Rong
    Wang, Shun-Yi
    Ji, Shun-Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (46) : 9471 - 9477
  • [2] A convenient synthesis of pyrrolo[3,4-c]quinolines
    Nyerges, N
    Virányi, A
    Töke, L
    HETEROCYCLIC COMMUNICATIONS, 2003, 9 (03) : 239 - 242
  • [3] A convenient synthesis of pyrrolo[3,4-c]quinolines
    Virányi, A
    Nyerges, M
    Blaskó, G
    Töke, L
    SYNTHESIS-STUTTGART, 2003, (17): : 2655 - 2660
  • [4] Pyrrolo[2,3-c]quinolines and pyrrolo[3,4-c]quinolines -: synthesis and investigation of lipoxygenase inhibition
    Görlitzer, K
    Fabian, J
    Frohberg, P
    Drutkowski, G
    PHARMAZIE, 2002, 57 (04): : 243 - 247
  • [5] NEW SYNTHESIS OF 2H-PYRROLO[3,4-C]QUINOLINES
    FRITZ, H
    SCHENK, S
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1975, (02): : 255 - 265
  • [6] 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
  • [7] SYNTHESIS OF PYRROLO[3,4-C]ISOQUINOLINEDIONES AND PYRROLO[3,4-C]BETA-CARBOLINEDIONE
    BOGZA, SL
    NIKOLYUKIN, YA
    ZUBRITSKII, MY
    DULENKO, VI
    ZHURNAL ORGANICHESKOI KHIMII, 1993, 29 (07): : 1480 - 1484
  • [8] A general, versatile synthesis of 2H-pyrrolo[3,4-c]quinolines via tosylmethylisocyanide reaction
    Di Santo, R
    Costi, R
    Forte, M
    Galeffi, C
    ARKIVOC, 2004, : 181 - 195
  • [9] Furo-, pyrrolo- and pyridazino[3,4-c]quinolines
    Gorlitzer, K
    Behrje, H
    PHARMAZIE, 1996, 51 (08): : 528 - 534
  • [10] SYNTHESIS OF PYRROLO[3,4-C]PYRIDAZINES
    POSCHENRIEDER, H
    STACHEL, HD
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (05) : 1457 - 1460