Titanium tetrachloride-mediated synthesis of N-aryl-substituted azacycles from cyclic ethers

被引:13
|
作者
Sun, Zunming
Hu, Shanshan
Huo, Yan
Wang, Zhihong [1 ]
机构
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
来源
RSC ADVANCES | 2017年 / 7卷 / 08期
关键词
ALKYNE HYDROAMINATION; BOND FORMATION; C-N; AMINES; COMPLEXES; EFFICIENT; AMINATION; CATALYST; ALCOHOLS; ROUTE;
D O I
10.1039/c6ra27325d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Titanium tetrachloride-mediated transformation of five- and six-membered cyclic ethers to the corresponding N-aryl-substituted azacycles is conducted in moderate to good yields under mild reaction conditions. Computational studies suggested a mechanism involving a Lewis acid-assisted ring-opening, a seven-membered metallacycle intermediate and a ring-closing process facilitated by direct participation of the metal center.
引用
收藏
页码:4363 / 4367
页数:5
相关论文
共 50 条
  • [41] On the Synthesis and Coordination Properties of N-Aryl-substituted 1, 3, 2-Diazaphospholidine-4, 5-diimines
    Mourgas, Georgios
    Tiritiris, Ioannis
    Nieger, Martin
    Gudat, Dietrich
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2013, 639 (3-4): : 517 - 523
  • [42] Effective synthesis of N-aryl-substituted 1,5,3-dithiazepinanes and 1,5,3-dithiazocinanes
    E. B. Rakhimova
    I. V. Vasil’yeva
    L. M. Khalilov
    A. G. Ibragimov
    U. M. Dzhemilev
    Chemistry of Heterocyclic Compounds, 2012, 48 : 1050 - 1057
  • [43] A general synthesis of substituted indoles from cyclic enol ethers and enol lactones
    Campos, KR
    Woo, JCS
    Lee, S
    Tillyer, RD
    ORGANIC LETTERS, 2004, 6 (01) : 79 - 82
  • [44] Synthesis of α,ω-differently substituted cyclic ethers from carbohydrates by β-fragmentation of alkoxyl radicals
    Boto, A
    Hernández, R
    Suárez, E
    TETRAHEDRON LETTERS, 2002, 43 (10) : 1821 - 1824
  • [45] Phosphine-Catalyzed Sequential Michael Addition between α-Aminonitriles and Methyl Acrylate for Cyclization: Synthesis of N-Aryl-Substituted Pyrrolidines
    H. C. Jang
    K. R. Sin
    H. R. Paek
    Y. M. Jang
    S. H. Jong
    Russian Journal of Organic Chemistry, 2020, 56 : 2228 - 2235
  • [46] Rhodium(I) Complexes of N-Aryl-Substituted Mono- and Bis(amidinates) Derived from Their Alkali Metal Salts
    Moos, Eric M. B.
    Gonzalez-Gallardo, Sandra
    Radius, Michael
    Breher, Frank
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2018, (26) : 3022 - 3035
  • [47] A new titanium tetrachloride mediated annulation of α-aryl-substituted carbonyl compounds with alkynes:: A simple and highly efficient method for the regioselective synthesis of polysubstituted naphthalene derivatives
    Kabalka, GW
    Ju, YH
    Wu, ZZ
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20): : 7915 - 7917
  • [48] Base-mediated synthesis of aryl enol ethers from α-aryl allylic alcohols and arylsulfonium salts
    Yao, Yu-Fei
    Song, Jia-Wei
    Zhang, Cheng-Pan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (38) : 7866 - 7873
  • [49] STUDY OF FURAN COMPOUNDS .50. SYNTHESIS OF N-ALKYL-SUBSTITUTED AND N-ARYL-SUBSTITUTED DIUREIDES OF 2,5-TETRAHYDROFURANDICARBONIC AND 2,5-TETRAHYDROTHIOPHENDICARBONIC ACIDS
    PONOMAREV, AA
    MARTEMYA.NI
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1971, (12): : 1587 - +
  • [50] Phosphine-Catalyzed Sequential Michael Addition between a-Aminonitriles and Methyl Acrylate for Cyclization: Synthesis of N-Aryl-Substituted Pyrrolidines
    Jang, H. C.
    Sin, K. R.
    Paek, H. R.
    Jang, Y. M.
    Jong, S. H.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (12) : 2228 - 2235