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
  • [11] Synthesis of 3-hetaryl-1,2,4,5-tetrahydropyrrolo-[1,2-a]quinazoline-2,5-diones
    Volovenko Yu.M.
    Resnyanskaya E.V.
    Tverdokhlebov A.V.
    Chemistry of Heterocyclic Compounds, 2002, 38 (3) : 324 - 330
  • [12] Synthesis of 3-hetaryl-1,2,4,5-tetrahydropyrrolo[1,2-α]quinazoline-2,5-diones
    Volovenko, YM
    Resnyanskaya, EV
    Tverdokhlebov, AV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (03): : 360 - 366
  • [13] A Three-Component Domino Reaction Enabled by Phase-Transfer Catalysis for the Assembly of 3-Thioquinoline-2,5-Diones
    Chen, Lin
    Zhu, Tian-Hao
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (06) : 1388 - 1396
  • [14] Iodine-catalyzed synthesis of 5-arylanthra[2,1-c][2,7]naphthyridine derivatives via three-component reaction
    Jiang, Hong
    Wang, Wei
    Wang, Xiang-Shan
    HETEROCYCLIC COMMUNICATIONS, 2012, 18 (03) : 151 - 155
  • [15] Iodine-catalyzed three-component annulation: access to highly fluorescent trisubstituted thiophenes
    Rajkumar, Deepan Babu
    Gnanaoli, Karthiyayini
    Puhazhendhi, Arulmozhi
    Arunachalam, Tamilselvi
    Nagarajan, Subbiah
    Sridharan, Vellaisamy
    Sivalingam, Soumya
    Maheswari, C. Uma
    CHEMICAL COMMUNICATIONS, 2023, 59 (67) : 10129 - 10132
  • [16] Molecular iodine-catalyzed imine activation for three-component nucleophilic addition reactions
    Lee, BS
    Mahajan, S
    Janda, KD
    SYNLETT, 2005, (08) : 1325 - 1327
  • [17] Three-component Mannich-type reaction catalyzed by iodine
    Kataki, Dolly
    Phukan, Prodeep
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2006, 45 (07): : 1759 - 1761
  • [18] Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes
    Kennedy-Ellis, Jonathan J.
    Boldt, Erik D.
    Chemler, Sherry R.
    ORGANIC LETTERS, 2020, 22 (21) : 8365 - 8369
  • [19] Iodine-catalyzed Povarov reaction for synthesis of cyclobuta[c]quinoline derivatives
    Yang, Jin-Ming
    Wu, Lin
    Fang, Dong
    Cao, Jian
    Zhou, Yu-Jing
    Wang, Xiang-Shan
    RESEARCH ON CHEMICAL INTERMEDIATES, 2014, 40 (03) : 1103 - 1113
  • [20] Iodine-catalyzed three-component one-pot synthesis of naphthopyranopyrimidines under solvent-free conditions
    Kumar, K. Praveen
    Satyanarayana, S.
    Reddy, P. Lakshmi
    Narasimhulu, G.
    Ravirala, Narender
    Reddy, B. V. Subba
    TETRAHEDRON LETTERS, 2012, 53 (14) : 1738 - 1741