Literature DB >> 19113815

Direct dehydrative N-pyridinylation of amides.

Jonathan William Medley1, Mohammad Movassaghi.   

Abstract

Electrophilic activation of secondary amides with trifluoromethanesulfonic anhydride in the presence of 2-fluoropyridine followed by introduction of a pyridine N-oxide derivative and warming affords the corresponding N-pyridinyl tertiary amide derivatives. A mechanism supported by in situ monitoring and deuterium labeling experiments is discussed.

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Year:  2009        PMID： 19113815     DOI： 10.1021/jo802355d

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  12 in total

1.  Triflic anhydride mediated synthesis of 3,4-dihydroquinazolines: a three-component one-pot tandem procedure.

Authors:  Christina L Magyar; Tyler J Wall; Steven B Davies; Molly V Campbell; Haven A Barna; Sydney R Smith; Christopher J Savich; R Adam Mosey
Journal:  Org Biomol Chem       Date:  2019-08-28       Impact factor: 3.876

2.  Direct Synthesis of Azaheterocycles from N-Aryl/Vinyl Amides. Synthesis of 4-(Methylthio)-2-phenylquinazoline and 4-(4-Methoxyphenyl)-2-phenylquinoline.

Authors:  Omar K Ahmad; Jonathan William Medley; Alexis Coste; Mohammad Movassaghi; Hiromi Kaise; Tohru Fukuyama
Journal:  Organic Synth       Date:  2012

3.  Electrophilic Carbonyl Activation: Competing Condensative Cyclizations of Tryptamine Derivatives.

Authors:  Fan Liu; Mohammad Movassaghi
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  Synthesis of spirocyclic indolines by interruption of the Bischler-Napieralski reaction.

Authors:  Jonathan William Medley; Mohammad Movassaghi
Journal:  Org Lett       Date:  2013-07-05       Impact factor: 6.005

5.  A concise and versatile double-cyclization strategy for the highly stereoselective synthesis and arylative dimerization of Aspidosperma alkaloids.

Authors:  Jonathan William Medley; Mohammad Movassaghi
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-12       Impact factor: 15.336

6.  Direct Observation of Intermediates Involved in the Interruption of the Bischler-Napieralski Reaction.

Authors:  Kolby L White; Marius Mewald; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2015-07-22       Impact factor: 4.354

7.  Chemoselective synthesis of ketones and ketimines by addition of organometallic reagents to secondary amides.

Authors:  William S Bechara; Guillaume Pelletier; André B Charette
Journal:  Nat Chem       Date:  2012-02-21       Impact factor: 24.427

8.  2-Aminopyridines via reaction of pyridine N-oxides and activated isocyanides.

Authors:  Mitchell Vamos; Nicholas D P Cosford
Journal:  J Org Chem       Date:  2014-02-18       Impact factor: 4.354

9.  Uniting Amide Synthesis and Activation by PIII/PV-Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines.

Authors:  Jeffrey M Lipshultz; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2021-09-03       Impact factor: 16.383

10.  Amidine dications as superelectrophiles.

Authors:  Michael J Corr; Mark D Roydhouse; Kirsty F Gibson; Sheng-Ze Zhou; Alan R Kennedy; John A Murphy
Journal:  J Am Chem Soc       Date:  2009-12-16       Impact factor: 15.419
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