A facile access to the 1,5-dihydro- and 1,3,4,5-tetrahydro-benzo[b]azepin-2-one ring systems via a new ring enlargement

被引:0
|
作者
Pauvert, M [1 ]
Dupont, V [1 ]
Guingant, A [1 ]
机构
[1] Fac Sci & Tech, Synth Organ Lab, F-44322 Nantes 03, France
关键词
quinolinium salt; silver nitrate; 1,5-dihydro-benzo[b]azepin-2-one; 1,3,4,5-tetrahydro-benzo[b] azepin-2-one; ring enlargement;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of a 1,5-dihydro-benzo[b]azepin-2-one is reported. The key reaction is a silver nitrate-induced rearrangement of N-benzyl quinolinium bromide. Its reduction leads to the 1,3,4,5-tetrahydro-benzo[b] azepin-2-one ring system found in several pharmacological important compounds.
引用
收藏
页码:1350 / 1352
页数:3
相关论文
共 50 条
  • [11] Epoxy resins based on the 1,2,3,4-tetrahydroquinoxaline and the 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine ring systems
    Davies, J
    Johncock, P
    Jones, DA
    POLYMER, 1999, 40 (17) : 4897 - 4906
  • [12] Benzimidazole condensed ring systems: New synthesis and antineoplastic activity of substituted 3,4-dihydro- and 1,2,3,4-tetrahydro-benzo[4,5]imidazo[1,2-a]pyrimidine derivatives
    Abdel-hafez, Atef Abdel-monem
    ARCHIVES OF PHARMACAL RESEARCH, 2007, 30 (06) : 678 - 684
  • [13] New synthesis of benzo[b][1,6]naphthyridines and pyrido[4,3-b]benz[f]azepines from lactim ethers of 3,4-dihydrocarbostyril and 1H-2,3,4,5-tetrahydrobenz[b]azepin-2-one
    Golovko, T. V.
    Smirnova, O. B.
    Solov'eva, N. P.
    Anisimova, O. S.
    Granik, V. G.
    RUSSIAN CHEMICAL BULLETIN, 2007, 56 (05) : 1032 - 1040
  • [14] New synthesis of benzo[b][1,6]naphthyridines and pyrido[4,3-b]benz[f]azepines from lactim ethers of 3,4-dihydrocarbostyril and 1H-2,3,4,5-tetrahydrobenz[b]azepin-2-one
    T. V. Golovko
    O. B. Smirnova
    N. P. Solov’eva
    O. S. Anisimova
    V. G. Granik
    Russian Chemical Bulletin, 2007, 56 : 1032 - 1040
  • [15] A facile hybrid 'flow and batch' access to substituted 3,4-dihydro-2H-benzo[b][1,4] oxazinones
    Lin, Andrew J. S.
    Russell, Cecilia C.
    Baker, Jennifer R.
    Frailey, Shelby L.
    Sakoff, Jennette A.
    McCluskey, Adam
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (37) : 8732 - 8742
  • [16] Synthesis, crystal structures and cytotoxic activity of new 1,3,4,5-tetrahydro-2H-1,5-benzodiazepine derivatives
    Faidallah, Hassan M.
    Taib, Layla A.
    Albeladi, Shams N. A.
    Rahman, Mohammed E. Ur
    Al-Zahrani, Fatimah Ali
    Arshad, Muhammad Nadeem
    Asiri, Abdullah M.
    JOURNAL OF CHEMICAL RESEARCH, 2015, (09) : 502 - 508
  • [17] (4Z)-1-Propargyl(1,3-Dipropargyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one
    Said, Ould Mohamed Sidya Mohamed
    Rachid, Bouhfid
    Joly, Nicolas
    Lequart, Vincent
    Martin, Patrick
    Massoui, M.
    Essassi, El Mokhtar
    MOLBANK, 2006, (05)
  • [18] (4Z)-1-Benzyl(1,3-Dibenzyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one
    Said, Ould Mohamed Sidya Mohamed
    Rachid, Bouhfid
    Joly, Nicolas
    Lequart, Vincent
    Martin, Patrick
    Massoui, M.
    Essassi, El Mokhtar
    MOLBANK, 2006, (05)
  • [19] Practical stereoselective synthesis of (2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)acetic acid
    Shinohara, T
    Kondo, K
    Ogawa, H
    Mori, T
    Nozaki, K
    Hiyama, T
    CHIRALITY, 2000, 12 (5-6) : 425 - 430
  • [20] Synthesis and anticonvulsant evaluation of some new 1,3,4,5-tetrahydro-6-alkoxy-2H-1-benzazepin-2-one derivatives
    Han, Rong-Bi
    Shao, Yun-Peng
    Wu, Hui-Fan
    Zhang, Duo
    Piao, Feng-Yu
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (06) : 2810 - 2820