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
  • [31] One-Pot Three-Component Synthesis of 4(3H)-Quinazolinones from Benzyl Halides, Isatoic Anhydride, and Primary Amines
    Adib, Mehdi
    Sheikhi, Ehsan
    Bijanzadeh, Hamid Reza
    SYNLETT, 2012, 23 (01) : 85 - 88
  • [32] Meglumine: A Novel and Efficient Catalyst for One-Pot, Three-Component Combinatorial Synthesis of Functionalized 2-Amino-4H-pyrans
    Guo, Rui-Yun
    An, Zhi-Min
    Mo, Li-Ping
    Wang, Rui-Zhi
    Liu, Hong-Xia
    Wang, Shu-Xia
    Zhang, Zhan-Hui
    ACS COMBINATORIAL SCIENCE, 2013, 15 (11) : 557 - 563
  • [33] A Facile Procedure for Synthesis of Several 1, 4, 5-Trisubstituted-1H-imidazole-2(3H)-ones and -thiones via a One-pot Three-portion Reaction in Solvent and Microwave Irradiation
    Shaker, Mohammad
    LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (02) : 104 - 109
  • [34] Cation-exchange resin as an efficient hetero-geneous catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones
    Wang, M.
    Zhang, T. T.
    Gao, J. J.
    Liang, Y.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (06) : 897 - 902
  • [35] Cation-exchange resin as an efficient hetero-geneous catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones
    M. Wang
    T. T. Zhang
    J. J. Gao
    Y. Liang
    Chemistry of Heterocyclic Compounds, 2012, 48 : 897 - 902
  • [36] Expedient one-pot three-component catalyst-free access to 5,6-dihydropyrimidin-4(3H)-one derivatives
    Ghandi, Mehdi
    Vazifeh, Maryam Jahangir
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2015, 12 (07) : 1131 - 1137
  • [37] CONVENIENT APPROACH FOR THE ONE-POT, THREE-COMPONENT SYNTHESIS OF TRIHETEROCYCLIC 4H-PYRIMIDO[2,1-b]BENZOTHIAZOLE DERIVATIVES USING TBAHS
    Nagarapu, Lingaiah
    Gaikwad, Hanmant K.
    Palem, Jyothsna Devi
    Venkatesh, Ramineni
    Bantu, Rajashaker
    Sridhar, B.
    SYNTHETIC COMMUNICATIONS, 2013, 43 (01) : 93 - 104
  • [38] Catalyst Free One-pot Three-component Synthesis of 2-Amino-4H-chromene Derivatives in Aqueous Deep Eutectic Mixture at Room Temperature
    Chaskar, Atul
    LETTERS IN ORGANIC CHEMISTRY, 2014, 11 (07) : 480 - 486
  • [39] Synthesis of 3-aminomethylidenechroman-2-carboxamides by a Sequential One-pot Three Component Reaction and by Post-Passerini Condensation Modification
    Ghosh, Jaydip
    Panja, Suman Kalyan
    Maiti, Sourav
    Biswas, Pritam
    Sarkar, Tapas
    Bandyopadhyay, Chandrakanta
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (02) : 449 - 456
  • [40] One-Pot, Three-Component Synthesis of Spironaphthopyrano[2,3-d]pyrimidine-5,3′-indolines in Water
    Ghahremanzadeh, Ramin
    Amanpour, Tayebeh
    Sayyafi, Maryam
    Bazgir, Ayoob
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (02) : 421 - 424