Nitrostyrenes as 1,4-CCNO-dipoles: diastereoselective formal [4+1] cycloaddition of indoles

被引:15
作者
Aksenov, Alexander V. [1 ]
Aksenov, Nicolai A. [1 ]
Aksenov, Dmitrii A. [1 ]
Khamraev, Vladislav F. [1 ]
Rubin, Michael [1 ,2 ]
机构
[1] North Caucasus Fed Univ, Dept Chem, 1a Pushkin St, Stavropol 355009, Russia
[2] Univ Kansas, Dept Chem, 1251 Wescoe Hall Dr, Lawrence, KS 66045 USA
基金
俄罗斯科学基金会;
关键词
EFFICIENT SYNTHESIS; BENZOXAZOLES; OXINDOLES; ROUTE;
D O I
10.1039/c8cc07451h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unusual reactivity of nitrostyrenes in phosphorous acid was discovered, which permits the employment of these readily available synthons as 1,4-CCNO-dipole surrogates in a highly diastereoselective (4+1)-cycloaddition of indoles to afford 4H-spiro[indole-3,5-isoxazoles] in a diastereomerically pure form.
引用
收藏
页码:13260 / 13263
页数:4
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共 26 条
  • [1] Direct reductive coupling of indoles to nitrostyrenes en route to (indol-3-yl)acetamides
    Aksenov, Alexander V.
    Aksenov, Nicolai A.
    Dzhandigova, Zarema V.
    Aksenov, Dmitrii A.
    Voskressensky, Leonid G.
    Nenajdenko, Valentine G.
    Rubin, Michael
    [J]. RSC ADVANCES, 2016, 6 (96) : 93881 - 93886
  • [2] An efficient synthesis of (3-indolyl)acetonitriles by reduction of hydroxamic acids
    Aksenov, Alexander V.
    Aksenov, Nicolai A.
    Dzhandigova, Zarema V.
    Aksenova, Inna V.
    Voskressensky, Leonid G.
    Smirnov, Alexander N.
    Rubin, Michael A.
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (05) : 299 - 302
  • [3] Nitroalkenes as surrogates for cyanomethylium species in a one-pot synthesis of non-symmetric diarylacetonitriles
    Aksenov, Alexander V.
    Aksenov, Nicolai A.
    Dzhandigova, Zarema V.
    Aksenov, Dmitrii A.
    Rubin, Michael
    [J]. RSC ADVANCES, 2015, 5 (129) : 106492 - 106497
  • [4] Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes
    Aksenov, Alexander V.
    Smirnov, Alexander N.
    Aksenov, Nicolai A.
    Bijieva, Asiyat S.
    Aksenova, Inna V.
    Rubin, Michael
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (14) : 4289 - 4295
  • [5] Activity of 2-Aryl-2-(3-indolyl)acetohydroxamates against Drug-Resistant Cancer Cells
    Aksenov, Alexander V.
    Smirnov, Alexander N.
    Magedov, Igor V.
    Reisenauer, Mary R.
    Aksenov, Nicolai A.
    Aksenova, Inna V.
    Pendleton, Alexander L.
    Gina Nguyen
    Johnston, Robert K.
    Rubin, Michael
    De Carvalho, Annelise
    Kiss, Robert
    Mathieu, Veronique
    Lefranc, Florence
    Correa, Jaime
    Cavazos, David A.
    Brenner, Andrew J.
    Bryan, Brad A.
    Rogelj, Snezna
    Kornienko, Alexander
    Frolova, Liliya V.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (05) : 2206 - 2220
  • [6] Metal-free ring expansion of indoles with nitroalkenes: a simple, modular approach to 3-substituted 2-quinolones
    Aksenov, Alexander V.
    Smirnov, Alexander N.
    Aksenov, Nicolai A.
    Aksenova, Inna V.
    Matheny, Jonathon P.
    Rubin, Michael
    [J]. RSC ADVANCES, 2015, 5 (12) : 8647 - 8656
  • [7] Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones
    Aksenov, Alexander V.
    Smirnov, Alexander N.
    Aksenov, Nicolai A.
    Aksenova, Inna V.
    Bijieva, Asiyat S.
    Rubin, Michael
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (48) : 9786 - 9788
  • [8] Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones
    Aksenov, Alexander V.
    Smirnov, Alexander N.
    Aksenov, Nicolai A.
    Aksenova, Inna V.
    Frolova, Liliya V.
    Kornienko, Alexander
    Magedov, Igor V.
    Rubin, Michael
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (81) : 9305 - 9307
  • [9] One-pot synthesis of benzoxazoles via the metal-free ortho-C-H functionalization of phenols with nitroalkanes
    Aksenov, Nicolai A.
    Aksenov, Alexander V.
    Nadein, Oleg N.
    Aksenov, Dmitrii A.
    Smirnov, Alexander N.
    Rubin, Michael
    [J]. RSC ADVANCES, 2015, 5 (88): : 71620 - 71626
  • [10] Copper-Catalyzed Selective N-Vinylation of 3-(Hydroxyimino)indolin-2-ones with Alkenyl Boronic Acids: Synthesis of N-Vinyl Nitrones and Spirooxindoles
    Chen, Chun-Hua
    Liu, Qing-Qing
    Ma, Xiao-Pan
    Feng, Yu
    Liang, Cui
    Pan, Cheng-Xue
    Su, Gui-Fa
    Mo, Dong-Liang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (12) : 6417 - 6425