Literature DB >> 19739609

Iron trichloride-promoted cyclization of o-alkynylaryl isocyanates: synthesis of 3-(chloromethylene)oxindoles.

Guillaume Cantagrel1, Benoît de Carné-Carnavalet, Christophe Meyer, Janine Cossy.   

Abstract

Iron trichloride promotes the cationic cyclization of o-(arylethynyl)aryl isocyanates leading to 3-(arylchloromethylene)oxindoles which can be stereoselectively converted to (Z)-3-(aminomethylene)oxindoles under straightforward conditions. When the alkyne is substituted by an alkyl group, activation of the allylic C-H bond also occurs producing 1,2-(dichloroalkylidene)oxindoles.

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Year:  2009        PMID: 19739609     DOI: 10.1021/ol9014877

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


  5 in total

1.  Mechanistic insights on the Pd-catalyzed addition of C-X bonds across alkynes - a combined experimental and computational study.

Authors:  Theresa Sperger; Christine M Le; Mark Lautens; Franziska Schoenebeck
Journal:  Chem Sci       Date:  2017-01-27       Impact factor: 9.825

Review 2.  Metal Fluorides, Metal Chlorides and Halogenated Metal Oxides as Lewis Acidic Heterogeneous Catalysts. Providing Some Context for Nanostructured Metal Fluorides.

Authors:  David Lennon; John M Winfield
Journal:  Molecules       Date:  2017-01-28       Impact factor: 4.411

3.  Expedient Synthesis of Indolo[2,3-b]quinolines, Chromeno[2,3-b]indoles, and 3-Alkenyl-oxindoles from 3,3'-Diindolylmethanes and Evaluation of Their Antibiotic Activity against Methicillin-Resistant Staphylococcus aureus.

Authors:  Chandrasekhar Challa; Jaice Ravindran; Mohini Mohan Konai; Sunil Varughese; Jubi Jacob; B S Dileep Kumar; Jayanta Haldar; Ravi S Lankalapalli
Journal:  ACS Omega       Date:  2017-08-30

4.  Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction.

Authors:  Lukáš Marek; Lukáš Kolman; Jiří Váňa; Jan Svoboda; Jiří Hanusek
Journal:  Beilstein J Org Chem       Date:  2021-02-23       Impact factor: 2.883

5.  The transient-chelating-group-controlled stereoselective Rh(i)-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to (Z)-3-(silylmethylene)indolin-2-ones.

Authors:  Ya-Fei Han; Gui-Fen Lv; Yang Li; Li-Jun Wu; Xuan-Hui Ouyang; Jin-Heng Li
Journal:  Chem Sci       Date:  2022-07-27       Impact factor: 9.969

  5 in total

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