Literature DB >> 24643619

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

Oleg V Larionov1, David Stephens, Adelphe M Mfuh, Hadi D Arman, Anastasia S Naumova, Gabriel Chavez, Behije Skenderi.   

Abstract

A Mo/P catalytic system for apan class="Chemical">n efficient gram-scale oxidation of a variety of nitrogen heterocycles to pan> class="Chemical">N-oxides with hydrogen peroxide as terminal oxidant has been investigated. Combined spectroscopic and crystallographic studies point to the tetranuclear Mo4P peroxo complex as one of the active catalytic species present in the solution. Based on this finding an optimized catalytic system has been developed. The utility and chemoselectivity of the catalytic system has been demonstrated by the synthesis of over 20 heterocyclic N-oxides.

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Year:  2014        PMID: 24643619      PMCID: PMC4134924          DOI: 10.1039/c4ob00115j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  34 in total

1.  A Survey of Applications of Polyoxometalates.

Authors:  Dimitris E. Katsoulis
Journal:  Chem Rev       Date:  1998-02-05       Impact factor: 60.622

2.  Enantioselective synthesis of sulfoxides: 2000-2009.

Authors:  Elzbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Chem Rev       Date:  2010-07-14       Impact factor: 60.622

3.  One-step conversion of azine N-oxides to alpha-1,2,4-triazolo-, 1,2,3-triazolo, imidazolo-, and pyrazoloheteroarenes.

Authors:  John M Keith
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

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

Authors:  Oleg V Larionov; David Stephens; Adelphe Mfuh; Gabriel Chavez
Journal:  Org Lett       Date:  2014-01-10       Impact factor: 6.005

6.  Molecular structure of the molybdenum oxo-diperoxo compound MoO(O(2))(2)(OPy)(H(2)O): a computational and X-ray study.

Authors:  F R Sensato; Q B Cass; E Longo; J Zukerman-Schpector; R Custodio; J Andrés; M Z Hernandes; R L Longo
Journal:  Inorg Chem       Date:  2001-11-05       Impact factor: 5.165

7.  Easy access to the family of thiazole N-oxides using HOF x CH3CN.

Authors:  Elizabeta Amir; Shlomo Rozen
Journal:  Chem Commun (Camb)       Date:  2006-04-25       Impact factor: 6.222

8.  New benzimidazole derivatives with potential cytotoxic activity--study of their stability by RP-HPLC.

Authors:  Katarzyna Błaszczak-Świątkiewicz; Marek Mirowski; Katarzyna Kaplińska; Rafał Kruszyński; Agata Trzęsowska-Kruszyńska; Elżbieta Mikiciuk-Olasik
Journal:  Acta Biochim Pol       Date:  2012-06-11       Impact factor: 2.149

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.  Sulfonylation of quinoline N-oxides with aryl sulfonyl chlorides via copper-catalyzed C-H bonds activation.

Authors:  Zhiyong Wu; Hongyu Song; Xiuling Cui; Chao Pi; Weiwei Du; Yangjie Wu
Journal:  Org Lett       Date:  2013-03-05       Impact factor: 6.005

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  9 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

Review 2.  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

3.  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

4.  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

5.  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

6.  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

7.  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

8.  Antiviral Activity of Novel Quinoline Derivatives against Dengue Virus Serotype 2.

Authors:  Carolina de la Guardia; David E Stephens; Hang T Dang; Mario Quijada; Oleg V Larionov; Ricardo Lleonart
Journal:  Molecules       Date:  2018-03-16       Impact factor: 4.411

Review 9.  Heteroaromatic N-Oxides in Asymmetric Catalysis: A Review.

Authors:  Zuzanna Wrzeszcz; Renata Siedlecka
Journal:  Molecules       Date:  2020-01-14       Impact factor: 4.411

  9 in total

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