An efficient oxa-Michael addition to diethyl vinylphosphonate under mild reaction conditions

被引:12
|
作者
Baszczynski, Ondrej [1 ]
Jansa, Petr [1 ]
Dracinsky, Martin [1 ]
Kaiser, Martin Maxmilian [1 ]
Spacek, Petr [1 ]
Janeba, Zlatko [1 ]
机构
[1] Acad Sci Czech Republic, Inst Organ Chem & Biochem, Vvi, CR-16610 Prague 6, Czech Republic
来源
RSC ADVANCES | 2012年 / 2卷 / 04期
关键词
ACYCLIC NUCLEOSIDE PHOSPHONATES; HYPOXANTHINE-GUANINE PHOSPHORIBOSYLTRANSFERASE; DERIVATIVES; INHIBITION; RESISTANCE; ANALOGS; TARGET; WATER; ACIDS; DNA;
D O I
10.1039/c2ra00938b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An oxa-Michael addition of various secondary and branched primary alcohols to diethyl vinylphosphonate was systematically studied and optimized. This efficient method precedes using of harsh reaction conditions (e.g. strong bases, high temperatures) and gains access to an important class of biologically active compounds in one step.
引用
收藏
页码:1282 / 1284
页数:3
相关论文
共 50 条
  • [21] Tandem nucleophilic addition-intramolecular oxa-Michael reaction: Novel synthetic route to trifluoromethylated phthalans
    Yuan, Hongling
    Gong, Yuefa
    JOURNAL OF FLUORINE CHEMISTRY, 2013, 149 : 125 - 129
  • [22] Electrosynthesis of Flavanones via oxa-Michael Addition Using Sacrificial Electrodes
    Santos, William A. B.
    de Castro, Pedro P.
    Xavier, Fernando R.
    Braga, Antonio L.
    Martins, Guilherme M.
    Mendes, Samuel R.
    SYNTHESIS-STUTTGART, 2023, 55 (18): : 2985 - 2992
  • [23] Tandem Nucleophilic Addition/Oxa-Michael Reaction for the Synthesis of cis-2,6-Disubstituted Tetrahydropyrans
    Gharpure, Santosh J.
    Prasad, J. V. K.
    Bera, Kalisankar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3570 - 3574
  • [24] Synthesis of Multisubstituted Indanedione Based Spiropyrans via Oxa-Michael/Michael Cascade Reaction
    Reddy, Yeruva Pavankumar
    Gudise, Veera Babu
    Settipalli, Poorna Chandrasekhar
    Anwar, Shaik
    CHEMISTRYSELECT, 2021, 6 (18): : 4456 - 4460
  • [25] The mechanism of the phosphine-catalyzed oxa-Michael reaction: a DFT investigation
    Suthar, Priyanka
    Singh, Ruchi
    Bansal, Raj K.
    STRUCTURAL CHEMISTRY, 2025,
  • [26] Recent advances in organocatalytic asymmetric oxa-Michael addition triggered cascade reactions
    Wang, Yu
    Du, Da-Ming
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (20) : 3266 - 3283
  • [27] Oxa-Michael addition polymerization of acrylates catalyzed by N-heterocyclic carbenes
    Matsuoka, Shin-ichi
    Namera, Shoko
    Suzuki, Masato
    POLYMER CHEMISTRY, 2015, 6 (02) : 294 - 301
  • [28] DNA-based catalytic enantioselective intermolecular oxa-Michael addition reactions
    Megens, Rik P.
    Roelfes, Gerard
    CHEMICAL COMMUNICATIONS, 2012, 48 (51) : 6366 - 6368
  • [29] Catalytic Enantioselective Intramolecular Oxa-Michael Reaction to α,β-Unsaturated Esters and Amides
    Su, Guanglong
    Formica, Michele
    Yamazaki, Ken
    Hamlin, Trevor A.
    Dixon, Darren J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (23) : 12771 - 12782
  • [30] Oxa-Michael/Ugi-Smiles cascade reaction with α,β-unsaturated aldehydes
    Thessing, Aubrey
    Ayres, Robert
    Jones, Joshua
    Bauer, Haleigh
    Zangi, Maryam
    Luesse, Sarah B.
    RESULTS IN CHEMISTRY, 2022, 4