Nitrile-Stabilized Quaternary Ammonium Ylide as an Arylcyanomethylene Transfer Agent: Diastereoselective Synthesis of Spiro-Cyanocyclopropyl-2-Oxindoles

被引:1
作者
Nagpure, Mithilesh [1 ]
Guchhait, Sankar K. [1 ]
机构
[1] Natl Inst Pharmaceut Educ & Res NIPER, Dept Med Chem, Sect 67, Mohali 160062, Punjab, India
关键词
Spirocyanocyclopropanation; Nitrile-stabilized quaternary ammonium ylide; Masked synthon; Spirocyanocylopropane oxindole; Diastereoselective; MEDIATED CYCLOPROPANATION; STEVENS REARRANGEMENT; OXINDOLES; IDENTIFICATION; INHIBITORS; DERIVATIVES; DISCOVERY; DESIGN; POTENT;
D O I
10.1002/ejoc.202400549
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitrile-stabilized quaternary ammonium ylide as an effective aryl-cyanomethylene transfer agent has been explored for the first time, which enables a spirocyclopropanation process with conjugated carboxamide of indole heterocycle. The developed In(OTf)3-catalyzed method provides a straightforward, diastereoselective access to pharmaceutically relevant spiro-cyclopropane-2-oxindole skeleton assembled with an alpha-cyano and two (hetero)aromatic substitutions. The common difficulties of a cyclopropanation process, e. g., a conjugated carboxamide as valid substrate, cleavage-susceptibility of amide bond, substrates scope limited to preferentially electron-withdrawing group containing molecules, and the competing dehydrocyanation reaction of product generated from nitrile-stabilized ylide have been overcome in the present spirocyclopropanation process. A diastereoselective cyclopropanation of nitrile-stabilized quaternary ammonium ylide with a weakly activated conjugated carboxamide functional motif is reported, which provides an efficient access to biologically relevant spiro-cyanocyclopropane oxindoles, while sigmatropic rearrangement process of the ylide is commonly known. image
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共 60 条
  • [1] Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes
    Almond-Thynne, Joshua
    Blakemore, David C.
    Pryde, David C.
    Spivey, Alan C.
    [J]. CHEMICAL SCIENCE, 2017, 8 (01) : 40 - 62
  • [2] Synthesis, Docking, and Bioavailability of 2′-Oxo-3-phenylspiro[cyclopropane-1,3′-indoline]-2,2-dicarbonitriles as Antibacterial Agents In Silico
    Avula, Vijay Kumar Reddy
    Chintha, Venkata Ramaiah
    Vallela, Swetha
    Anireddy, Jaya Shree
    Chamarthi, Naga Raju
    Wudayagiri, Rajendra
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (01) : 209 - 217
  • [3] Bhattacharjee S., 1982, SYNTHESIS-STUTTGART, V1982, P301
  • [4] α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles
    Caiuby, Clarice A. D.
    de Jesus, Matheus P.
    Burtoloso, Antonio C. B.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11) : 7433 - 7445
  • [5] RuII-Catalyzed/NH2-Assisted Selective Alkenyl C-H [5+1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines
    Chen, Pu
    Nan, Jiang
    Hu, Yan
    Ma, Qiong
    Ma, Yangmin
    [J]. ORGANIC LETTERS, 2019, 21 (12) : 4812 - 4815
  • [6] Rh(III)-Catalyzed Cascade Reactions of Sulfoxonium Ylides with α-Diazocarbonyl Compounds: An Access to Highly Functionalized Naphthalenones
    Chen, Xi
    Wang, Muhua
    Zhang, Xinying
    Fan, Xuesen
    [J]. ORGANIC LETTERS, 2019, 21 (08) : 2541 - 2545
  • [7] Microwave induced formal [2+1] Michael-cyclization cascade sequence of 3-ylidene oxindoles and pyridinium phenacyl salts
    Chimaladenne, Venkateswarlu
    Surapureddi, Rama Krishna
    Valluru, Krishna Reddy
    Kampli, Anil
    Brahman, Pradeep Kumar
    Laxmi, Somarapu Vijaya
    [J]. SYNTHETIC COMMUNICATIONS, 2022, 52 (11-12) : 1357 - 1367
  • [8] Discovery of Sisunatovir (RV521), an Inhibitor of Respiratory Syncytial Virus Fusion
    Cockerill, G. Stuart
    Angell, Richard M.
    Bedernjak, Alexandre
    Chuckowree, Irina
    Fraser, Ian
    Gascon-Simorte, Jose
    Gilman, Morgan S. A.
    Good, James A. D.
    Harland, Rachel
    Johnson, Sara M.
    Ludes-Meyers, John H.
    Littler, Edward
    Lumley, James
    Lunn, Graham
    Mathews, Neil
    McLellan, Jason S.
    Paradowski, Michael
    Peeples, Mark E.
    Scott, Claire
    Tait, Dereck
    Taylor, Geraldine
    Thom, Michelle
    Thomas, Elaine
    Barber, Carol Villalonga
    Ward, Simon E.
    Watterson, Daniel
    Williams, Gareth
    Young, Paul
    Powell, Kenneth
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2021, 64 (07) : 3658 - 3676
  • [9] Dolak A., 2021, CATALYSTS, V11, P439, DOI DOI 10.3390/CATAL11040439
  • [10] Enantioselective Ammonium Ylide Mediated One-Pot Synthesis of Highly Substitutedγ-Butyrolactones
    Drennhaus, Till
    Oehler, Laura
    Djalali, Saveh
    Hoefmann, Svenja
    Mueller, Clemens
    Pietruszka, Joerg
    Worgull, Dennis
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (12) : 2385 - 2396