Literature DB >> 24410049

Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides.

Oleg V Larionov1, David Stephens, Adelphe Mfuh, Gabriel Chavez.   

Abstract

A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.

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Year:  2014        PMID： 24410049      PMCID： PMC4134923          DOI： 10.1021/ol403631k

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


  38 in total

1.  Characteristic physical properties and structural fragments of marketed oral drugs.

Authors:  Michal Vieth; Miles G Siegel; Richard E Higgs; Ian A Watson; Daniel H Robertson; Kenneth A Savin; Gregory L Durst; Philip A Hipskind
Journal:  J Med Chem       Date:  2004-01-01       Impact factor: 7.446

2.  Recent developments in the field of organic heterobimetallic compounds of the alkaline-earth metals.

Authors:  Matthias Westerhausen
Journal:  Dalton Trans       Date:  2006-09-05       Impact factor: 4.390

3.  A strategy for C-H activation of pyridines: direct C-2 selective alkenylation of pyridines by nickel/Lewis acid catalysis.

Authors:  Yoshiaki Nakao; Kyalo Stephen Kanyiva; Tamejiro Hiyama
Journal:  J Am Chem Soc       Date:  2008-02-05       Impact factor: 15.419

4.  Palladium-catalyzed cross-coupling reactions of diazine N-oxides with aryl chlorides, bromides, and iodides.

Authors:  Jean-Philippe Leclerc; Keith Fagnou
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

5.  Facile one-pot direct arylation and alkylation of nitropyridine N-oxides with Grignard reagents.

Authors:  Fang Zhang; Xin-Fang Duan
Journal:  Org Lett       Date:  2011-10-27       Impact factor: 6.005

6.  Efficient, mild and completely regioselective synthesis of substituted pyridines.

Authors:  Hans Andersson; Thomas Sainte-Luce Banchelin; Sajal Das; Roger Olsson; Fredrik Almqvist
Journal:  Chem Commun (Camb)       Date:  2010-03-16       Impact factor: 6.222

7.  Palladium-catalyzed sequential formation of C-C bonds: efficient assembly of 2-substituted and 2,3-disubstituted quinolines.

Authors:  Xiaochen Ji; Huawen Huang; Yibiao Li; Huoji Chen; Huanfeng Jiang
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-13       Impact factor: 15.336

8.  Complete regioselective addition of grignard reagents to pyrazine N-oxides, toward an efficient enantioselective synthesis of substituted piperazines.

Authors:  Hans Andersson; Thomas Sainte-Luce Banchelin; Sajal Das; Magnus Gustafsson; Roger Olsson; Fredrik Almqvist
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

9.  Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors:  Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

10.  TMEDA-assisted effective direct ortho arylation of electron-deficient N-heteroarenes with aromatic Grignard reagents.

Authors:  Fang-Fang Zhuo; Wen-Wen Xie; Yong-Xin Yang; Lei Zhang; Pei Wang; Rui Yuan; Chao-Shan Da
Journal:  J Org Chem       Date:  2013-03-19       Impact factor: 4.354
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  12 in total

1.  Experimental and mechanistic analysis of the palladium-catalyzed oxidative C8-selective C-H homocoupling of quinoline N-oxides.

Authors:  David E Stephens; Johant Lakey-Beitia; Gabriel Chavez; Carla Ilie; Hadi D Arman; Oleg V Larionov
Journal:  Chem Commun (Camb)       Date:  2015-06-11       Impact factor: 6.222

2.  Organocatalytic Synthesis of Methylene-Bridged N-Heterobiaryls.

Authors:  David E Stephens; Vu T Nguyen; Bhuwan Chhetri; Emily R Clark; Hadi D Arman; Oleg V Larionov
Journal:  Org Lett       Date:  2016-11-03       Impact factor: 6.005

Review 3.  Heterocyclic N-Oxides - An Emerging Class of Therapeutic Agents.

Authors:  A M Mfuh; O V Larionov
Journal:  Curr Med Chem       Date:  2015       Impact factor: 4.530

4.  Mechanistic insights into the potassium tert-butoxide-mediated synthesis of N-heterobiaryls.

Authors:  David E Stephens; Johant Lakey-Beitia; Jessica E Burch; Hadi D Arman; Oleg V Larionov
Journal:  Chem Commun (Camb)       Date:  2016-08-02       Impact factor: 6.222

5.  Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides.

Authors:  David E Stephens; Gabriel Chavez; Martin Valdes; Monica Dovalina; Hadi D Arman; Oleg V Larionov
Journal:  Org Biomol Chem       Date:  2014-07-03       Impact factor: 3.876

6.  Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  Tetrahedron       Date:  2015-08-19       Impact factor: 2.457

7.  Insights into the structural patterns of the antileishmanial activity of bi- and tricyclic N-heterocycles.

Authors:  Lizzi Herrera; David E Stephens; Abigail D'Avila; Kathryn G George; Hadi Arman; Yu Zhang; George Perry; Ricardo Lleonart; Oleg V Larionov; Patricia L Fernández
Journal:  Org Biomol Chem       Date:  2016-07-04       Impact factor: 3.876

8.  Insights into the mechanistic and synthetic aspects of the Mo/P-catalyzed oxidation of N-heterocycles.

Authors:  Oleg V Larionov; David Stephens; Adelphe M Mfuh; Hadi D Arman; Anastasia S Naumova; Gabriel Chavez; Behije Skenderi
Journal:  Org Biomol Chem       Date:  2014-05-21       Impact factor: 3.876

9.  Palladium-Catalyzed C8-Selective C-H Arylation of Quinoline N-Oxides: Insights into the Electronic, Steric and Solvation Effects on the Site-Selectivity by Mechanistic and DFT Computational Studies.

Authors:  David E Stephens; Johant Lakey-Beitia; Abdurrahman C Atesin; Tülay A Ateşin; Gabriel Chavez; Hadi D Arman; Oleg V Larionov
Journal:  ACS Catal       Date:  2015-01-02       Impact factor: 13.084

10.  Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.

Authors:  Peng Zhang; Andrea M Cook; Yang Liu; Christian Wolf
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354
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