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
  • [41] Efficient synthesis of 2-amino-3-cyano-4H-pyran derivatives via a non-catalytic one-pot three-component reaction
    Lu, Cheng-Wei
    Wang, Jia-Jing
    Li, Fei
    Yu, Shi-Jun
    An, Yue
    RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (02) : 1035 - 1043
  • [42] A facile one-pot three component synthesis of 3, 4-dihydropyrimidin-2(1H)-ones or thiones promoted by a polymer-supported BF3 under solvent-free conditions
    Zarchi, Mohammad Ali Karimi
    Hajati, Farhad
    Mirjalili, Bibi Fatemeh
    RESEARCH ON CHEMICAL INTERMEDIATES, 2022, 48 (08) : 3449 - 3473
  • [43] One-pot three-component synthesis of 3-Amino-5,8-dioxo-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazines
    Adib, Mehdi
    Koloogani, Somayeh Aali
    Abbasi, Alireza
    Bijanzadeh, Hamid Reza
    SYNTHESIS-STUTTGART, 2007, (19): : 3056 - 3060
  • [44] Nickel-catalyzed One-pot, Three-component Synthesis of 3,4-disubstituted Isoxazole-5(4H)-ones in Aqueous Medium
    Kiyani, Hamzeh
    Samimi, Heshmat Allah
    CHIANG MAI JOURNAL OF SCIENCE, 2017, 44 (03): : 1011 - 1021
  • [45] "In-Water" Three-Component One-Pot Reaction for the Facile Synthesis of Densely Functionalized 2,3-Dihydro-1H-pyrrol-2-ols and Mechanistic Insight
    Saigal, Nallakantham
    Sudheer, Nallakantham
    Sahoo, Subash C.
    Khan, Md. Musawwer
    Seth, Kapileswar
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2024, 12 (35): : 13336 - 13351
  • [46] Triphenylsulfophosphonium chlorometallates as efficient heterogeneous catalysts for the three-component synthesis of 2,3-dihydro-1,2,3-trisubstituted-1H-naphth[1,2-e][1,3]oxazines
    Dutta, Arup Kumar
    Gogoi, Pinky
    Borah, Ruli
    POLYHEDRON, 2017, 123 : 184 - 191
  • [47] Synthesis of Highly Substituted 4H-Pyrido[1,2-a]pyrimidines via a One-Pot Three-Component Condensation Reaction
    Yang, Kai
    Xiang, Jinbao
    Bao, Guochen
    Dang, Qun
    Bai, Xu
    ACS COMBINATORIAL SCIENCE, 2013, 15 (09) : 519 - 524
  • [48] Recyclable bimetallic CuFe2O4 nanoparticles: an efficient catalyst for one-pot three-component synthesis of novel dicyanomethyl-2-oxoindolin-3-ylthiocarboxylic acids in a green solvent
    Shakibaei, Ghazaleh Imani
    Ghahremanzadeh, Ramin
    Bazgir, Ayoob
    MONATSHEFTE FUR CHEMIE, 2014, 145 (06): : 1009 - 1015
  • [49] One-pot three-component synthesis of pyrido [2′,1′: 2,3] imidazo[4,5-c] isoquinolines using Fe3O4@SiO2-OSO3H as an efficient heterogeneous nanocatalyst
    Maleki, Ali
    RSC ADVANCES, 2014, 4 (109): : 64169 - 64173
  • [50] T3P catalyzed one pot three-component synthesis of 2,3-disubstituted 3H-quinazolin-4-ones
    Raghavendra, Goravanahalli M.
    Kumar, Chottanahalli S. Pavan
    Suresha, Gejjalagere P.
    Rangappa, Kanchugarakoppal S.
    Mantelingu, Kempegowda
    CHINESE CHEMICAL LETTERS, 2015, 26 (08) : 963 - 968