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Literature DB >> 32043885

Cyanomethylation of Substituted Fluorenes and Oxindoles with Alkyl Nitriles.

Gang Hong¹, Pradip D Nahide¹, Marisa C Kozlowski¹.

Abstract

The first example of metal-free cyanomethylenation from alkyl nitriles of sp3 C-H bonds to afford quaternary carbon centers is described. This oxidative protocol is operationally simple and features good functional group compatibility. This method provides a novel approach to highly functionalized fluorene and oxindole derivatives, which are commonly used in material and pharmaceutical areas. Control experiments provide evidence of a radical reaction process.

Entities: Chemical Disease Gene Species

Mesh：

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Year: 2020 PMID： 32043885 PMCID： PMC7036039 DOI： 10.1021/acs.orglett.0c00160

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

53 in total

1. N-(3-fluoro-4-(4-(2-methoxy or 2,3-dichlorophenyl)piperazine-1-yl)butyl)arylcarboxamides as selective dopamine D3 receptor ligands: critical role of the carboxamide linker for D3 receptor selectivity.

Authors: Ashwini K Banala; Benjamin A Levy; Sameer S Khatri; Cheryse A Furman; Rebecca A Roof; Yogesh Mishra; Suzy A Griffin; David R Sibley; Robert R Luedtke; Amy Hauck Newman
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2. Radical reactivity of aza[60]fullerene: preparation of monoadducts and limitations.

Authors: Georgios C Vougioukalakis; Manolis M Roubelakis; Michael Orfanopoulos
Journal: J Org Chem Date: 2010-06-18 Impact factor: 4.354

3. Radical Changes in Lewis Acid Catalysis: Matching Metal and Substrate.

Authors: Tim Bleith; Qing-Hai Deng; Hubert Wadepohl; Lutz H Gade
Journal: Angew Chem Int Ed Engl Date: 2016-06-02 Impact factor: 15.336

4. Transition-Metal-Free Alkynylation of 2-Oxindoles through Radical-Radical Coupling.

Authors: Hong-Yan Huang; Liang Cheng; Jie-Jie Liu; Dong Wang; Li Liu; Chao-Jun Li
Journal: J Org Chem Date: 2017-02-16 Impact factor: 4.354

Review 5. The mitomycin bioreductive antitumor agents: cross-linking and alkylation of DNA as the molecular basis of their activity.

Authors: M Tomasz; Y Palom
Journal: Pharmacol Ther Date: 1997 Oct-Dec Impact factor: 12.310

6. Phosphonium salts as chiral phase-transfer catalysts: asymmetric Michael and Mannich reactions of 3-aryloxindoles.

Authors: Rongjun He; Changhua Ding; Keiji Maruoka
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

7. Synthesis and biological evaluation of (-)- and (+)-debromoflustramine B and its analogues as selective butyrylcholinesterase inhibitors.

Authors: Ernesto Rivera-Becerril; Pedro Joseph-Nathan; Víctor M Pérez-Alvarez; Martha S Morales-Ríos
Journal: J Med Chem Date: 2008-08-08 Impact factor: 7.446

Cyanomethylation of Substituted Fluorenes and Oxindoles with Alkyl Nitriles.

1. N-(3-fluoro-4-(4-(2-methoxy or 2,3-dichlorophenyl)piperazine-1-yl)butyl)arylcarboxamides as selective dopamine D3 receptor ligands: critical role of the carboxamide linker for D3 receptor selectivity.

2. Radical reactivity of aza[60]fullerene: preparation of monoadducts and limitations.

3. Radical Changes in Lewis Acid Catalysis: Matching Metal and Substrate.

4. Transition-Metal-Free Alkynylation of 2-Oxindoles through Radical-Radical Coupling.

Review 5. The mitomycin bioreductive antitumor agents: cross-linking and alkylation of DNA as the molecular basis of their activity.

6. Phosphonium salts as chiral phase-transfer catalysts: asymmetric Michael and Mannich reactions of 3-aryloxindoles.

7. Synthesis and biological evaluation of (-)- and (+)-debromoflustramine B and its analogues as selective butyrylcholinesterase inhibitors.

8. Copper-mediated/catalyzed oxyalkylation of alkenes with alkylnitriles.

9. Chemoselective activation of sp(3) vs sp(2) C-H bonds with Pd(II).

10. Palladium-catalyzed ligand-promoted site-selective cyanomethylation of unactivated C(sp³)-H bonds with acetonitrile.

1. Construction of sterically congested oxindole derivatives via visible-light-induced radical-coupling.

2. A computational study for the reaction mechanism of metal-free cyanomethylation of aryl alkynoates with acetonitrile.

3. Direct Oxidation of Aryl Malononitriles Enabling a Copper-Catalyzed Intermolecular Alkene Carbochlorination.