An Efficient Protocol for the Synthesis of Carboacyclic Nucleosides via Aza-Conjugate Addition Reaction

被引:0
|
作者
Zolfigol, Mohammad Ali [1 ]
Khazaei, Ardeshir [1 ]
Moosavi-Zare, Ahmad Reza [1 ]
Zare, Abdolkarim [2 ]
Hasanijejad, Ali Reza [3 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Hamadan, Iran
[2] PNU, Dept Chem, Tehran, Iran
[3] Persian Gulf Univ, Fac Sci, Dept Chem, Bushehr, Iran
关键词
Carboacyclic nucleoside; Aza-conjugate addition reaction; Pyrimidine nucleobase; alpha; beta-unsaturated ester; Microwave; MICHAEL ADDITION; ALPHA; BETA-UNSATURATED ESTERS; PURINE NUCLEOBASES; HIGHLY EFFICIENT; PYRIMIDINE; CATALYST; GREEN; DERIVATIVES; SOLVENT;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new efficient method for the synthesis of carboacyclic nucleosides as biologically interesting compounds via aza-conjugate addition of pyrimidine nucleobases to alpha,beta-unsaturated esters in the presence of catalytic amount of LiOH center dot H2O (1.2-4.8 mol%) under microwave irradiation is described. This method affords the title compounds in good to excellent yields and in short reaction times. [GRAPHICS]
引用
收藏
页码:67 / 73
页数:7
相关论文
共 50 条
  • [21] Ionic liquid-accelerated Michael addition of pyrimidine and purine nucleobases to α,β-unsaturated esters: a rapid approach to carboacyclic nucleosides synthesis
    Zare, Abdolkarim
    Hasaninejad, Alireza
    Safinejad, Roholla
    Moosavi-Zare, Ahmad Reza
    Khalafi-Nezhad, Ali
    Beyzavi, Mohammad Hassan
    Miralai-Moredi, Mojtaba
    Dehghani, Esmail
    Kazerooni-Mojarrad, Parvin
    ARKIVOC, 2008, : 61 - 74
  • [22] Total synthesis of clavosolide A via tandem allylic oxidation/oxa-conjugate addition reaction
    Baker, Joseph B.
    Kim, Hyoungsu
    Hong, Jiyong
    TETRAHEDRON LETTERS, 2015, 56 (23) : 3120 - 3122
  • [23] STEREOSELECTIVE SYNTHESIS OF CEMBRANOLIDES VIA CONJUGATE ADDITION TO CYCLOALKYNONES
    MARSHALL, JA
    CROOKS, SL
    TETRAHEDRON LETTERS, 1987, 28 (43) : 5081 - 5082
  • [24] Effect of Superbasic Ionic Liquids on the Synthesis of Dendritic Polyamines via Aza-Michael Addition Reaction
    Bereska, Bartlomiej
    Czaja, Krystyna
    Nowicki, Janusz
    Ilowska, Jolanta
    Bereska, Agnieszka
    Muszynski, Marcin
    Szmatola, Michal
    Grabowski, Rafal
    CHEMISTRYSELECT, 2017, 2 (31): : 10020 - 10026
  • [25] A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-Michael reaction in water
    Matveeva, Ekaterina V.
    Petrovskii, Pavel V.
    Klemenkova, Zinaida S.
    Bondarenko, Natalya A.
    Odinets, Irina L.
    COMPTES RENDUS CHIMIE, 2010, 13 (8-9) : 964 - 970
  • [26] Synthesis of γ-lactam lignans via aza-Michael addition
    Dorbec, M
    Florent, JC
    Monneret, C
    Rager, MN
    Bertounesque, E
    SYNLETT, 2006, (04) : 591 - 594
  • [27] Efficient Synthesis of Fused Pyrimidine Derivatives with Biological Activity via Aza-Wittig Reaction
    Ren Qingyun
    Tan Xiaosong
    He Hongwu
    CURRENT ORGANIC SYNTHESIS, 2011, 8 (05) : 752 - 763
  • [28] A PRACTICAL AND EFFICIENT GREEN SYNTHESIS OF β-AMINOPHOSPHORYL COMPOUNDS VIA THE AZA-MICHAEL REACTION IN WATER
    Matveeva, Ekaterina V.
    Shipov, Anatoly E.
    Odinets, Irina L.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (04) : 698 - 706
  • [29] Synthesis of Chiral Acyclic Pyrimidine Nucleosides with a Sulfur-Containing Side Chain via Enantioselective Tandem Conjugate Addition/Protonation
    Li, Jian-Ping
    Tuo, Hao-Ran
    Xie, Ming-Sheng
    Kang, Bo
    Qu, Gui-Rong
    Guo, Hai-Ming
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (01) : 128 - 132
  • [30] Efficient synthesis of (±)-γ-lycorane employing stereoselective conjugate addition to nitroolefin
    Yasuhara, T
    Osafune, E
    Nishimura, K
    Yamashita, M
    Yamada, K
    Muraoka, O
    Tomioka, K
    TETRAHEDRON LETTERS, 2004, 45 (15) : 3043 - 3045