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
  • [1] (E)-5-(Methoxyimino)-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one
    Ihnatenko, Irina
    Jones, Peter G.
    Kunick, Conrad
    MOLBANK, 2021, 2021 (04)
  • [2] Classical and dynamic resolution of 1-amino-3-methyl-1,3,4,5-tetrahydrobenzo[d]azepin-2-one
    Mitchell, D
    Hay, LA
    Koenig, TM
    McDaniel, S
    Nissen, JS
    Audia, JE
    TETRAHEDRON-ASYMMETRY, 2005, 16 (23) : 3814 - 3819
  • [3] Computational and spectral studies of 3,3′-(propane-1,3-diyl) bis(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one)
    Kumar, S. Anil
    Bhaskar, B. L.
    HELIYON, 2019, 5 (09)
  • [4] Regioselective alkylation of 1,3,4,5-tetrahydrobenzo[d]azepin-2-one and biological evaluation of the resulting alkylated products as potentially selective agonists
    Prajapati, Navnit
    Giridhar, Rajani
    Sinha, Anshuman
    Kanhed, Ashish M.
    Yadav, Mange Ram
    MOLECULAR DIVERSITY, 2015, 19 (04) : 653 - 667
  • [5] UNSATURATED HETEROCYCLIC SYSTEMS .26. NEW ASPECTS OF PHENOXIDE ION TO 1,3-DIHYDRO-2H-AZEPIN-2-ONE RING EXPANSION
    PAQUETTE, LA
    FARLEY, WC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (14) : 3595 - &
  • [6] FACILE SYNTHESIS OF NOVEL 3-QUINOXALINYL-1,5-BENZODIAZEPINES VIA RING TRANSFORMATION - STABLE TAUTOMERS IN THE 1,5-BENZODIAZEPIN-2-ONE RING-SYSTEM
    KURASAWA, Y
    OKAMOTO, Y
    OGURA, K
    TAKADA, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (03) : 661 - 664
  • [7] A NEW SYNTHETIC METHOD FOR PREPARATION OF 1,3,4,5-TETRAHYDRO-2H-1-BENZAZEPIN-2-ONE DERIVATIVES
    ITO, Y
    KOBAYASHI, K
    MAENO, M
    SAEGUSA, T
    CHEMISTRY LETTERS, 1980, (05) : 487 - 490
  • [8] Synthesis and Anticonvulsant Activity of 3-(alkylamino, alkoxy)-1,3,4,5-Tetrahydro-2H-benzo [b] azepine-2-one Derivatives
    Huang, Xia
    Chen, Tie
    Han, Rong-Bi
    Piao, Feng-Yu
    CNS & NEUROLOGICAL DISORDERS-DRUG TARGETS, 2018, 17 (06) : 448 - 457
  • [9] Facile synthesis of substituted 2,3,4,7-tetrahydro-1H-azepines via ring-closing metathesis
    Brass, S
    Gerber, HD
    Dörr, S
    Diederich, WE
    TETRAHEDRON, 2006, 62 (08) : 1777 - 1786
  • [10] 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]pyrinnidine derivatives
    Atef Abdel-monem Abdel-hafez
    Archives of Pharmacal Research, 2007, 30