Mild Organic Ammonium Tribromide-Mediated Regioselective Ring Opening of Epoxides with Alcohols, Water, Acetic Anhydride, and Amines Under Solvent-Free Reaction Conditions

被引:12
|
作者
Singhal, Sweety [1 ]
Jain, Suman L. [1 ]
Sain, Bir [1 ]
机构
[1] Indian Inst Petr, Council Sci & Ind Res, Div Chem Sci, Dehra Dun 248005, Uttar Pradesh, India
关键词
Metal free; MPHT; regioselective synthesis; ring opening; solid bromine; CARBONYL-COMPOUNDS; REUSABLE CATALYST; EFFICIENT; BROMINATION; PROTOCOL; ACID; OATB;
D O I
10.1080/00397911.2010.493259
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[image omitted] Organic ammonium tribromide (OATB), N-methylpyrrolidine-2-one hydrotribromide (MPHT) was found to be an efficient catalyst for the regioselective ring opening of epoxides with various nucleophiles under solvent free conditions. This procedure occurs under neutral and mild reaction conditions with out adding any additive and afforded high yields of products.
引用
收藏
页码:1829 / 1837
页数:9
相关论文
共 26 条
  • [1] Catalyst-free regioselective ring opening of epoxides with aromatic amines in water and solvent-free conditions
    Ziyaei-Halimehjani, A.
    Gholami, H.
    Saidi, M. R.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2013, 10 (01) : 7 - 11
  • [2] Catalyst-free regioselective ring opening of epoxides with aromatic amines in water and solvent-free conditions
    A. Ziyaei-Halimehjani
    H. Gholami
    M. R. Saidi
    Journal of the Iranian Chemical Society, 2013, 10 : 7 - 11
  • [3] Highly regioselective ring-opening of epoxides with amines: a metal- and solvent-free protocol for the synthesis of β-amino alcohols
    Li, Dong
    Wang, Jing
    Yu, Shibo
    Ye, Silei
    Zou, Wenjie
    Zhang, Hongbin
    Chen, Jingbo
    CHEMICAL COMMUNICATIONS, 2020, 56 (15) : 2256 - 2259
  • [4] Efficient method for ring opening of epoxides with amines by NaY zeolite under solvent-free conditions
    Kureshy, Rukhsana Ilyas
    Singh, Surendra
    Khan, Noor-ul Hasan
    Abdi, Sayed Hasan Razi
    Suresh, Eringathodi
    Jasra, Raksh Vir
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 264 (1-2) : 162 - 169
  • [5] Regioselective Ring Opening of Epoxides with Amines Using Silica-bonded S-sulfonic Acid under Solvent-free Conditions
    Tajbakhsh, Mahmood
    Hosseinzadeh, Rahman
    Rezaee, Parizad
    Alinezhad, Heshmatollah
    JOURNAL OF THE MEXICAN CHEMICAL SOCIETY, 2012, 56 (04) : 402 - 407
  • [6] Regioselective Ring-Opening of Aziridines and Epoxides with Amines under Catalyst- and Solvent-Free Condition on Solid Phase
    Li, Wanmei
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2012, 34 (03): : 669 - 672
  • [7] Highly Regioselective Ring Opening of Epoxides with Thiols Catalyzed by SbCl3 Under Solvent-Free Conditions
    Ghazanfari, Dadkhoda
    Hashemi, Mohammed M.
    Akhgar, Mohammad Reza
    Foroughi, Mohammad Mehdi
    Najafi-Zadeh, Fariba
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (12) : 3018 - 3022
  • [8] Zn(OAc)2/podand catalyzed ring opening of epoxides by aromatic amines under solvent-free conditions
    Eshghi, H.
    Rahimizadeh, M.
    Shoryabi, A.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2005, 2 (02) : 155 - 160
  • [9] Modified Montmorillonite clay catalyzed regioselective ring opening of epoxide with amines and alcohols under solvent free conditions
    Bhuyan, Diganta
    Saikia, Lakshi
    Dutta, Dipak Kumar
    APPLIED CATALYSIS A-GENERAL, 2014, 487 : 195 - 201
  • [10] Zn(OAc)2/podand catalyzed ring opening of epoxides by aromatic amines under solvent-free conditions
    H. Eshghi
    M. Rahimizadeh
    A. Shoryabi
    Journal of the Iranian Chemical Society, 2005, 2 : 155 - 160