Literature DB >> 17500567

A general and efficient 2-amination of pyridines and quinolines.

Jingjun Yin1, Bangping Xiang, Mark A Huffman, Conrad E Raab, Ian W Davies.   

Abstract

Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the same manner. Combined with the simple oxidation of pyridines to pyridine N-oxides, this method provides a general and efficient way for amination of 2-unsubstituted pyridines.

Entities:  

Mesh：

Substances：

Year:  2007        PMID： 17500567     DOI： 10.1021/jo070189y

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


  16 in total

1.  Hydrophilic, Potent, and Selective 7-Substituted 2-Aminoquinolines as Improved Human Neuronal Nitric Oxide Synthase Inhibitors.

Authors:  Anthony V Pensa; Maris A Cinelli; Huiying Li; Georges Chreifi; Paramita Mukherjee; Linda J Roman; Pavel Martásek; Thomas L Poulos; Richard B Silverman
Journal:  J Med Chem       Date:  2017-08-04       Impact factor: 7.446

2.  Nitrile in the Hole: Discovery of a Small Auxiliary Pocket in Neuronal Nitric Oxide Synthase Leading to the Development of Potent and Selective 2-Aminoquinoline Inhibitors.

Authors:  Maris A Cinelli; Huiying Li; Georges Chreifi; Thomas L Poulos; Richard B Silverman
Journal:  J Med Chem       Date:  2017-04-19       Impact factor: 7.446

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.  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

5.  A Strategy to Aminate Pyridines, Diazines, and Pharmaceuticals via Heterocyclic Phosphonium Salts.

Authors:  Chirag Patel; Margaret Mohnike; Michael C Hilton; Andrew McNally
Journal:  Org Lett       Date:  2018-04-17       Impact factor: 6.005

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.  Core Replacements in a Potent Series of VEGFR-2 Inhibitors and Their Impact on Potency, Solubility, and hERG.

Authors:  Nello Mainolfi; James Powers; Erik Meredith; Jason Elliott; Karl G Gunderson; Stephen Poor; Fang Liu; Karen Anderson
Journal:  ACS Med Chem Lett       Date:  2016-03-16       Impact factor: 4.345

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.  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

10.  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
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.