Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 2-Aminopyridines via reaction of pyridine N-oxides and activated isocyanides.

Literature DB >> 24490824

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

Abstract

A practical and efficient method for the synthesis of substituted 2-aminopyridines from pyridine N-oxides is reported. Yields of purified, isolated products of up to 84% are observed for the one-pot, two-step process. The reaction involves an in situ deprotection of an isolable N-formylaminopyridine intermediate and facilitates the synthesis of 2-aminopyridines for which other methods fail.

Entities: CellLine Chemical Disease Species

Mesh：

Substances：

Year: 2014 PMID： 24490824 PMCID： PMC4374735 DOI： 10.1021/jo402693s

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

15 in total

1. Structure-activity relationship study of prion inhibition by 2-aminopyridine-3,5-dicarbonitrile-based compounds: parallel synthesis, bioactivity, and in vitro pharmacokinetics.

Authors: Barnaby C H May; Julie A Zorn; Juanita Witkop; John Sherrill; Andrew C Wallace; Giuseppe Legname; Stanley B Prusiner; Fred E Cohen
Journal: J Med Chem Date: 2007-01-11 Impact factor: 7.446

2. Discovery of N-(4-(2-amino-3-chloropyridin-4-yloxy)-3-fluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (BMS-777607), a selective and orally efficacious inhibitor of the Met kinase superfamily.

Authors: Gretchen M Schroeder; Yongmi An; Zhen-Wei Cai; Xiao-Tao Chen; Cheryl Clark; Lyndon A M Cornelius; Jun Dai; Johnni Gullo-Brown; Ashok Gupta; Benjamin Henley; John T Hunt; Robert Jeyaseelan; Amrita Kamath; Kyoung Kim; Jonathan Lippy; Louis J Lombardo; Veeraswamy Manne; Simone Oppenheimer; John S Sack; Robert J Schmidt; Guoxiang Shen; Kevin Stefanski; John S Tokarski; George L Trainor; Barri S Wautlet; Donna Wei; David K Williams; Yingru Zhang; Yueping Zhang; Joseph Fargnoli; Robert M Borzilleri
Journal: J Med Chem Date: 2009-03-12 Impact factor: 7.446

3. 3,5-Diaryl-2-aminopyridines as a novel class of orally active antimalarials demonstrating single dose cure in mice and clinical candidate potential.

Authors: Yassir Younis; Frederic Douelle; Tzu-Shean Feng; Diego González Cabrera; Claire Le Manach; Aloysius T Nchinda; Sandra Duffy; Karen L White; David M Shackleford; Julia Morizzi; Janne Mannila; Kasiram Katneni; Ravi Bhamidipati; K Mohammed Zabiulla; Jayan T Joseph; Sridevi Bashyam; David Waterson; Michael J Witty; David Hardick; Sergio Wittlin; Vicky Avery; Susan A Charman; Kelly Chibale
Journal: J Med Chem Date: 2012-03-21 Impact factor: 7.446

4. Synthesis of unsymmetrically substituted bipyridines by palladium-catalyzed direct C-H arylation of pyridine N-oxides.

Authors: Sasa Duric; C Christoph Tzschucke
Journal: Org Lett Date: 2011-04-01 Impact factor: 6.005

5. General and mild preparation of 2-aminopyridines.

Authors: Allyn T Londregan; Sandra Jennings; Liuqing Wei
Journal: Org Lett Date: 2010-10-19 Impact factor: 6.005

6. Expedient synthesis of highly potent antagonists of inhibitor of apoptosis proteins (IAPs) with unique selectivity for ML-IAP.

Authors: Mitchell Vamos; Kate Welsh; Darren Finlay; Pooi San Lee; Peter D Mace; Scott J Snipas; Monica L Gonzalez; Santhi Reddy Ganji; Robert J Ardecky; Stefan J Riedl; Guy S Salvesen; Kristiina Vuori; John C Reed; Nicholas D P Cosford
Journal: ACS Chem Biol Date: 2013-02-05 Impact factor: 5.100

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

1. Structure-activity relationship study of prion inhibition by 2-aminopyridine-3,5-dicarbonitrile-based compounds: parallel synthesis, bioactivity, and in vitro pharmacokinetics.

2. Discovery of N-(4-(2-amino-3-chloropyridin-4-yloxy)-3-fluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (BMS-777607), a selective and orally efficacious inhibitor of the Met kinase superfamily.

3. 3,5-Diaryl-2-aminopyridines as a novel class of orally active antimalarials demonstrating single dose cure in mice and clinical candidate potential.

4. Synthesis of unsymmetrically substituted bipyridines by palladium-catalyzed direct C-H arylation of pyridine N-oxides.

5. General and mild preparation of 2-aminopyridines.

6. Expedient synthesis of highly potent antagonists of inhibitor of apoptosis proteins (IAPs) with unique selectivity for ML-IAP.

7. One-step conversion of azine N-oxides to α-N-aryltriflamidoazines.

8. Reaction of aromatic N-oxides with dipolarophiles. I. Reaction products of 3-picoline 1-oxide with phenyl isocyanate.

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

10. Benzimidazole N-oxides. IV. 1,3-dipolar cycloaddition reaction with 1-methylbenzimidazole 3-oxide.

1. Synthesis and Fluorescent Properties of Aminopyridines and the Application in "Click and Probing".