Iodine-catalyzed three-component reaction of quinazoline-2,5-diones with aldehydes and styrenes for the synthesis of allylamine derivatives

被引:8
|
作者
Zhang, Zhang [1 ,2 ]
Zhang, Yu-Shan [1 ,2 ]
Quan, Zheng-Jun [1 ,2 ]
Da, Yu-Xia [1 ,2 ]
Wang, Xi-Cun [1 ,2 ]
机构
[1] Minist Educ, Key Lab Ecoenvironm Related Polymer Mat, Lanzhou 730070, Gansu, Peoples R China
[2] Northwest Normal Univ, Coll Chem & Chem Engn, Gansu Key Lab Polymer Mat, Lanzhou 730070, Peoples R China
基金
中国国家自然科学基金;
关键词
Iodine; Allyamines; Three-component reaction; C-C formation; C-N formation; ALLYLIC AMINATION; REDUCTIVE AMINATION; EFFICIENT SYNTHESIS; 1ST EXAMPLES; ARYLATION; ALCOHOLS; HETEROCYCLES; CYCLIZATION; MECHANISMS; 1,3-DIENES;
D O I
10.1016/j.tet.2014.10.006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iodine-catalyzed three component reaction of quinazoline-2,5-diones, aldehydes, and styrenes provides allylamine derivatives was described. Both paraformaldehyde and ethyl glyoxalate can be applied in this reaction with simple styrenes with high regioselectivity. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9093 / 9098
页数:6
相关论文
共 50 条
  • [31] SYNTHESIS OF QUINAZOLINE DERIVATIVES BY THE [4+2] CYCLOADDITION OF 2,1-BENZISOXAZOLES WITH 3-IMIDAZOLINE-2,5-DIONES
    OHTA, K
    NAKAMURA, Y
    IWAOKA, J
    NOMURA, Y
    NIPPON KAGAKU KAISHI, 1990, (01) : 72 - 83
  • [32] Bronsted-Acid-Catalyzed Asymmetric Three-Component Reaction of Amines, Aldehydes, and Pyruvate Derivatives. Enantioselective Synthesis of Highly Functionalized γ-Lactam Derivatives
    del Corte, Xabier
    Maestro, Aitor
    Vicario, Javier
    Martinez de Marigorta, Edorta
    Palacios, Francisco
    ORGANIC LETTERS, 2018, 20 (02) : 317 - 320
  • [33] Enantioselective, copper(I) -catalyzed three-component reaction for the synthesis of β,γ-alkynyl α-amino acid derivatives
    Shao, Zhihui
    Pu, Xuewei
    Li, Xiaojiao
    Fan, Baomin
    Chan, Albert S. C.
    TETRAHEDRON-ASYMMETRY, 2009, 20 (02) : 225 - 229
  • [34] Synthesis of Spiro Pyrrolobenzothiazole Derivatives via a Three-Component Reaction
    Nassiri, M.
    Milani, F. J.
    Hassankhani, A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (04) : 1162 - 1166
  • [35] Direct Synthesis of 2,5-Disubstituted Oxazoles through an Iodine-Catalyzed Decarboxylative Domino Reaction
    Xu, Wei
    Kloeckner, Ulrich
    Nachtsheim, Boris J.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12): : 6065 - 6074
  • [36] Fluoride-catalyzed three-component coupling reaction of a silylphosphine, activated alkenes and aldehydes
    Hayashi, M
    Matsuura, Y
    Watanabe, Y
    TETRAHEDRON LETTERS, 2005, 46 (31) : 5135 - 5138
  • [37] Titanocene(III)-Catalyzed Three-Component Reaction of Secondary Amides, Aldehydes, and Electrophilic Alkenes
    Zheng, Xiao
    He, Jiang
    Li, Heng-Hui
    Wang, Ao
    Dai, Xi-Jie
    Wang, Ai-E
    Huang, Pei-Qiang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) : 13739 - 13742
  • [38] Sequential catalytic process:: synthesis of quinoline derivatives by AuCl3/CuBr-catalyzed three-component reaction of aldehydes, amines, and alkynes
    Xiao, Fengping
    Chen, Yulin
    Liu, Yu
    Wang, Jianbo
    TETRAHEDRON, 2008, 64 (12) : 2755 - 2761
  • [39] Iron-Catalyzed Three-Component Synthesis of α-Amino Acid Derivatives
    Halli, Juliette
    Manolikakes, Georg
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (33) : 7471 - 7475
  • [40] Efficient, Three-Component Synthesis of Pyrrole Derivatives Catalyzed by Iodobenzene and Oxone
    Jagadhane, Prashant B.
    Jadhav, Nikhil C.
    Herlekar, Omkar P.
    Telvekar, Vikas N.
    SYNTHETIC COMMUNICATIONS, 2015, 45 (18) : 2130 - 2134