Convenient synthesis of substituted benzo[e][1,2,4]- or [d][1,2,6] oxadiazepines, benzo[f][1,3,5]triazocines from N-aryliminoesters

被引:3
|
作者
Saied, Tarak [1 ,2 ]
Jelaiel, Nourchaine [2 ]
Efrit, Mohamed Lotfi [2 ]
Fort, Yves [1 ]
Comoy, Corinne [1 ]
机构
[1] Univ Lorraine, SRSMC UMR CNRS 7565, Grp Heterocycles React & Interact HecRIn, BP 239,Blvd Aiguillettes, F-54506 Vandoeuvre Les Nancy, France
[2] Fac Sci Tunis, Dept Chim, Lab Synth Organ & Heterocycl, El Manar Tunis 2092, Tunisia
关键词
Condensed ring system; Nitrogen heterocycles; Benzoxadiazepines; Benzotriazocines; Synthetic method; RING; BENZOTHIADIAZOCINES; BENZOXADIAZOCINES; BENZOTRIAZOCINES; REARRANGEMENT; HETEROCYCLES; DERIVATIVES;
D O I
10.1016/j.tet.2017.01.063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report herein a short and efficient synthesis of benz[e][1,2,4]- or [d][1,2,6]oxadiazepines and benzo[f] [1,3,5]triazocines from easily prepared N-aryl iminoesters. The strategy involves a bis-nucleophile reagent (hydroxylamine or guanidine) that promotes a one-step ring closure from the starting functionalized iminoesters. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1489 / 1494
页数:6
相关论文
共 50 条
  • [21] A convenient synthesis of 1,2,4-triazolo-1,3,5-triazin-4-ones and 1,2,4-triazolo-1,3,5-triazin-4-thiones
    Abderrahim, Raoudha
    Boujlel, Khaled
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (05) : 995 - 999
  • [22] Application of the aza-Wittig reaction for efficient synthesis of diversely substituted benzo[f]Chromeno[2,3-d]pyrimidine and benzo[f]chromeno[2,3-d][1,2,4]triazolopyrimidine derivatives
    Hassan, Mohamed
    Barsy, Magda A.
    El Rady, Eman A.
    Al-Ayed, Abdullah Sulaiman
    Frempong, Mona
    Sadek, Kamal U.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (04) : 543 - 549
  • [23] [3+3] Cyclocondensation of β-carbonyl-substituted 1H-benzo[f]chromenes with 3-amino-1,2,4-triazoles: synthesis of [1,2,4] triazolo [1,5-a] pyrimidines
    Osipov, Dmitry, V
    Korzhenko, Kirill S.
    Osyanin, Vitaly A.
    Krasnikov, Pavel E.
    Klimochkin, Yuri N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2022, 58 (11) : 651 - 655
  • [24] [3+3] Cyclocondensation of β-carbonyl-substituted 1H-benzo[f]chromenes with 3-amino-1,2,4-triazoles: synthesis of [1,2,4]triazolo[1,5-a]pyrimidines
    Dmitry V. Osipov
    Kirill S. Korzhenko
    Vitaly A. Osyanin
    Pavel E. Krasnikov
    Yuri N. Klimochkin
    Chemistry of Heterocyclic Compounds, 2022, 58 : 651 - 655
  • [25] Convenient Synthesis of Substituted Quinoxalines and 2H-Benzo[b][1,4]oxazines in Water
    Ding Chang-jiang
    Wang Yan
    Zhang Wei-wei
    Liu Li
    Liang Yong-jiu
    Dong De-wen
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2009, 25 (02) : 174 - 177
  • [26] Convenient Synthesis of Substituted Quinoxalines and 2H-Benzo[b][1,4]oxazines in Water
    DING Chang-jiang1
    2. Changchun Institute of Applied Chemistry
    Chemical Research in Chinese Universities, 2009, 25 (02) : 174 - 177
  • [27] Facile synthesis of substituted benzo[d]pyrrolo[2ʹ,3ʹ:4,5]pyrrolo[1,2-a]imidazoles by 2-(1H-benzo[d]imidazol-2-yl)acetonitrile and arylglyoxals
    Farzaneh Alizadeh-Bami
    Hossein Mehrabi
    Reza Ranjbar-Karimi
    Monatshefte für Chemie - Chemical Monthly, 2022, 153 : 913 - 918
  • [28] Recent advances in the chemistry of benzo[e][1,2,4]triazinyl radicals
    Rogers, Fergus J. M.
    Norcott, Philip L.
    Coote, Michelle L.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (41) : 8255 - 8277
  • [29] Facile synthesis of substituted benzo[d]pyrrolo[2′,3′:4,5] pyrrolo[1,2-a]imidazoles by 2-(1H-benzo[d]imidazol-2-yl)acetonitrile and arylglyoxals
    Alizadeh-Bami, Farzaneh
    Mehrabi, Hossein
    Ranjbar-Karimi, Reza
    MONATSHEFTE FUR CHEMIE, 2022, 153 (10): : 913 - 918
  • [30] Synthesis of New Derivatives Benzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidine
    A. A. Harutyunyan
    G. T. Gukasyan
    H. A. Panosyan
    R. A. Tamazyan
    A. G. Ayvazyan
    A. S. Grigoryan
    G. G Danagulyan
    Russian Journal of Organic Chemistry, 2019, 55 : 1698 - 1703