Literature DB >> 21375291

Mild addition of nucleophiles to pyridine-N-oxides.

Allyn T Londregan1, Sandra Jennings, Liuqing Wei.   

Abstract

A general and facile one-pot procedure for the synthesis of 2-substituted pyridines from the corresponding pyridine-N-oxides and nucleophiles is presented as a mild alternative to S(N)Ar chemistry. A variety of nucleophiles and heterocyclic-N-oxides participate effectively in this transformation, which uses the phosphonium salt, PyBroP, as a means of substrate activation.

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Year:  2011        PMID： 21375291     DOI： 10.1021/ol200352g

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


  16 in total

1.  Generation of diverse 1-imidazolylisoquinolines via silver triflate-catalyzed reaction of 2-alkynylbenzaldoxime with imidazole.

Authors:  Qian Xiao; Shengqing Ye; Danqing Zheng; Ling Zhang; Jie Wu
Journal:  Mol Divers       Date:  2012-01-25       Impact factor: 2.943

2.  Reduction of amine N-oxides by diboron reagents.

Authors:  Hari Prasad Kokatla; Paul F Thomson; Suyeal Bae; Venkata Ramana Doddi; Mahesh K Lakshman
Journal:  J Org Chem       Date:  2011-08-31       Impact factor: 4.354

3.  Construction of pyrazolo[3,4-b]pyridines and pyrazolo[4,3-c]pyridines by ring closure of 3-acylpyridine N-oxide tosylhydrazones.

Authors:  William J Lominac; Megan L D'Angelo; Mark D Smith; Darius A Ollison; James M Hanna
Journal:  Tetrahedron Lett       Date:  2012-02-22       Impact factor: 2.415

4.  Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones.

Authors:  Timothy J Donohoe; Ben S Pilgrim; Geraint R Jones; José A Bassuto
Journal:  Proc Natl Acad Sci U S A       Date:  2012-07-02       Impact factor: 11.205

Review 5.  Synthesis and Transformations of NH-Sulfoximines.

Authors:  Michael Andresini; Arianna Tota; Leonardo Degennaro; James A Bull; Renzo Luisi
Journal:  Chemistry       Date:  2021-10-13       Impact factor: 5.020

6.  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

7.  Catalytic Enantioselective Pyridine N-Oxidation.

Authors:  Sheng-Ying Hsieh; Yu Tang; Simone Crotti; Elizabeth A Stone; Scott J Miller
Journal:  J Am Chem Soc       Date:  2019-11-12       Impact factor: 15.419

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.  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.  The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16'-epi-Leucophyllidine.

Authors:  Christopher E Reimann; Aurapat Ngamnithiporn; Kohei Hayashida; Daisuke Saito; Katerina M Korch; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-06       Impact factor: 16.823
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