Novel approach for the synthesis of N-unsubstituted 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones

被引:0
|
作者
Alexander V. Borisov
Svitlana S. Kovalenko
Sergiy M. Kovalenko
机构
[1] Latvian Institute of Organic Synthesis,
[2] Enamine Ltd.,undefined
[3] National University of Pharmacy,undefined
[4] V. N. Karazin Kharkiv National University,undefined
来源
关键词
lortalamine; 2,6-methano-1,3-benzoxazocine-4-thiones; 6-methano-1,3-benzoxazocin-4-one; pyridoxal; tandem reaction;
D O I
暂无
中图分类号
学科分类号
摘要
An efficient one-pot method for the synthesis of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones in high yields has been developed via regioselective tandem reaction of coumarin-3-thioamides and ketones containing different methylene groups. Further oxidation with hydrogen peroxide under basic conditions leads to the formation of N-unsubstituted derivatives of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocin-4-one.
引用
收藏
页码:678 / 681
页数:3
相关论文
共 50 条
  • [41] 2-Methyl-11-nitro-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one: synthesis, crystal structure and tautomerism in dipolar aprotic solvents
    Sedova, Valentina F.
    Krivopalov, Viktor P.
    Gatilov, Yurii V.
    Shkurko, Oleg P.
    MENDELEEV COMMUNICATIONS, 2013, 23 (03) : 176 - 178
  • [42] Novel Synthesis of Tryptamine Derived 4-Hydroxy-4-arylthiazolidine-2-thiones and 4-Arylthiazole-2(3H)-thiones by Multicomponent Reactions
    Devi, Nepram Sushuma
    Singh, Sarangthem Joychandra
    Mahiya, Kuldeep
    Singh, Okram Mukherjee
    Choi, Hojune
    Lee, Sang-Gyeong
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (09): : 1472 - 1477
  • [43] Novel rearrangement of a 2-aryl-3-alkyl-3H-indol-3-ol to a 1,4,5,6-tetrahydro-2,6-methano-1-benzazocin-3(2H)-one with implications for the biosynthesis of aspernomine
    Liu, YH
    McWhorter, WW
    Hadden, CE
    ORGANIC LETTERS, 2003, 5 (03) : 333 - 335
  • [44] Two approaches toward the regio- and stereoselective synthesis of N-unsubstituted 3-aryl-4-(trifluoromethyl)-4H-spiro-[chromeno[3,4-c]pyrrolidine-1,3′-oxindoles]
    Korotaev, Vladislav Yu
    Barkovskii, Savelii, V
    Kutyashev, Igor B.
    Ulitko, Maria, V
    Barkov, Alexey Yu
    Zimnitskiy, Nikolay S.
    Kochnev, Ivan A.
    Sosnovskikh, Vyacheslav Ya
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (06) : 679 - 690
  • [45] Sequential 5(4H)-oxazolone cycloaddition and nitrile oxide addition reactions with 4-arylmethyleneisoxazol-5-ones:: Regioselective synthesis of N-unsubstituted pyrrole hydroxamate derivatives
    Grassi, G
    Risitano, F
    Foti, F
    Cordaro, M
    SYNLETT, 2001, (06) : 812 - 814
  • [46] SYNTHESIS AND ANALGESIC ACTIVITY OF 4-(CYCLOPROPYLMETHYL)-3,4,5,6-TETRAHYDRO-2H-1,5-METHANO-1,4-BENZODIAZOCIN-9-AMINE
    GUBITZ, FW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1981, 182 (AUG): : 27 - MEDI
  • [47] SYNTHESIS AND REACTIONS OF 2-(ALKYLTHIO)-4,4-DIMETHYL-1,3-THIAZOLE-5(4H)-THIONES
    SHI, JX
    LINDEN, A
    HEIMGARTNER, H
    HELVETICA CHIMICA ACTA, 1994, 77 (07) : 1903 - 1920
  • [48] Unexpected transformations of 11-acetyl-8-bromo-2-methyl-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one(thione)
    Valentina F. Sedova
    Viktor P. Krivopalov
    Oleg P. Shkurko
    Chemistry of Heterocyclic Compounds, 2017, 53 : 1163 - 1166
  • [49] [2 + 3] Cycloadditions of Azomethine Ylides with 1,3-Thiazole-5(4H)-thiones
    Mloston, G.
    Linden, A.
    Heimgartner, H.
    Helvetica Chimica Acta, 81 (03):
  • [50] Unexpected transformations of 11-acetyl-8-bromo-2-methyl-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one(thione)
    Sedova, Valentina F.
    Krivopalov, Viktor P.
    Shkurko, Oleg P.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (10) : 1163 - 1166