Ytterbium Triflate Promoted One-Pot Three Component Synthesis of 3,4,5-Trisubstituted-3,6-dihydro-2H-1,3-oxazines

被引:13
|
作者
Epifano, Francesco [2 ]
Pelucchini, Caroline [1 ]
Rosati, Ornelio [1 ]
Genovese, Salvatore [2 ]
Curini, Massimo [1 ]
机构
[1] Univ Perugia, Dipartimento Chim & Tecnol Farmaco, Sez Chim Organ, I-06123 Perugia, Italy
[2] Univ G dAnnunzio, Dipartimento Sci Farmaco, I-66100 Chieti, CH, Italy
关键词
Heterogeneous catalysis; Multicomponent reactions; Lanthanides; Oxazine derivatives; Ytterbium triflate; MULTICOMPONENT REACTIONS; 3-COMPONENT SYNTHESIS; DOMINO REACTIONS; CHEMISTRY; BOND;
D O I
10.1007/s10562-011-0605-3
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An efficient one-pot synthesis of 3,4,5-trisubstituted-3,6-dihydro-2H-1,3-oxazines from acetylene dicarboxylates, aromatic and aliphatic amines, and formaldehyde is described. The six member N,O-heterocyclic nucleus was constructed via Yb(OTf)(3) promoted domino hydroamination/Prins reaction/cyclization/dehydration reactions.
引用
收藏
页码:844 / 849
页数:6
相关论文
共 50 条
  • [1] Ytterbium Triflate Promoted One-Pot Three Component Synthesis of 3,4,5-Trisubstituted-3,6-dihydro-2H-1,3-oxazines
    Francesco Epifano
    Caroline Pelucchini
    Ornelio Rosati
    Salvatore Genovese
    Massimo Curini
    Catalysis Letters, 2011, 141 : 844 - 849
  • [2] Bronsted acid-promoted domino reactions: a novel one-pot three-component synthesis of 3,4,5-trisubstituted-3,6-dihydro-2H-1,3-oxazines
    Cao, Hua
    Jiang, Huan-Feng
    Qi, Chao-Rong
    Yao, Wen-Juan
    Chen, Huo-Ji
    TETRAHEDRON LETTERS, 2009, 50 (11) : 1209 - 1214
  • [3] Multicomponent Synthesis of 3,6-Dihydro-2H-1,3-thiazine-2-thiones
    Kruithof, Art
    Ploeger, Marten L.
    Janssen, Elwin
    Helliwell, Madeleine
    de Kanter, Frans J. J.
    Ruijter, Eelco
    Orru, Romano V. A.
    MOLECULES, 2012, 17 (02) : 1675 - 1685
  • [4] One-pot, three-component synthesis of 1-amidomethyl-imidazo[1,2-a]pyridines catalyzed by ytterbium triflate
    Pericherla, Kasiviswanadharaju
    Khungar, Bharti
    Kumar, Anil
    TETRAHEDRON LETTERS, 2012, 53 (10) : 1253 - 1257
  • [5] Synthesis of 2-amino-4H-1,3-oxazines and 2-amino-4H-1,3-thiazines through a Yb(OTf)3-assisted, acid-catalyzed one-pot cyclocondensation reaction
    Putatunda, Salil
    Chakraborty, Arijit
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (08) : 763 - 768
  • [6] Synthesis of 2-amino-4H-1,3-oxazines and 2-amino-4H-1,3-thiazines through a Yb(OTf)3-assisted, acid-catalyzed one-pot cyclocondensation reaction
    Salil Putatunda
    Arijit Chakraborty
    Chemistry of Heterocyclic Compounds, 2015, 51 : 763 - 768
  • [7] Synthesis of Trisubstituted 1H-Pyrazole-4-carbodithioates in a One-Pot Three-Component Reaction Catalyzed by Ferric Sulfate
    Khan, Abu T.
    Ghosh, Arindam
    Basha, Sidick R.
    Mir, Mohammad Hedayetullah
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (02) : 126 - 129
  • [8] Three-Component, One-Pot Sequential Synthesis of Functionalized Cyclazines: 3H-1,2a1,3-Triazaacenaphthylenes
    Sun, Hongpeng
    Zhou, Huayong
    Khorev, Oleg
    Jiang, Ruwei
    Yu, Ting
    Wang, Xin
    Du, Yongli
    Ma, Yi
    Meng, Tao
    Shen, Jingkang
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (23) : 10745 - 10751
  • [9] One-Pot Synthesis of 2,3,5-Trisubstituted Thiophenes through Three-Component Assembly of Arylacetaldehydes, Elemental Sulfur, and 1,3-Dicarbonyls
    Wang, Zilong
    Qu, Zhonghua
    Xiao, Fuhong
    Huang, Huawen
    Deng, Guo-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 796 - 800
  • [10] One-Pot Multicomponent Domino Synthesis of 4-Aminothiazole-2(3H)-thiones
    Hajibabaei, Khadijeh
    Zali-Boeini, Hassan
    SYNLETT, 2015, 26 (01) : 108 - 110