Literature DB >> 25165405

A mild, catalyst-free synthesis of 2-aminopyridines.

Bhaskar Poola1, Wonken Choung2, Michael H Nantz1.   

Abstract

Alkylation of 2-mercaptopyridine with 1,2-dibromoethane affords a cyclic dihydrothiazolopyridinium salt that can serve as a precursor of 2-aminopyridines. Its reaction with primary or secondary amines, either neat or in DMSO, under mild conditions gives the title compounds.

Entities:  

Keywords:  N-alkyl pyridinium; aminopyridine; heteroaryl amine; thiazolopyridinium

Year:  2008        PMID： 25165405      PMCID： PMC4143138          DOI： 10.1016/j.tet.2008.09.010

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  19 in total

1.  The Synthesis of Aminopyridines: A Method Employing Palladium-Catalyzed Carbon-Nitrogen Bond Formation.

Authors:  Seble Wagaw; Stephen L. Buchwald
Journal:  J Org Chem       Date:  1996-10-18       Impact factor: 4.354

2.  A convenient synthesis of 2-(alkylamino)pyridines.

Authors:  Douglas M Krein; Todd L Lowary
Journal:  J Org Chem       Date:  2002-07-12       Impact factor: 4.354

3.  An air and thermally stable one- component catalyst for the amination of aryl chlorides.

Authors:  Danilo Zim; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

4.  Design, synthesis, and evaluation of inhibitors for severe acute respiratory syndrome 3C-like protease based on phthalhydrazide ketones or heteroaromatic esters.

Authors:  Jianmin Zhang; Hanna I Pettersson; Carly Huitema; Chunying Niu; Jiang Yin; Michael N G James; Lindsay D Eltis; John C Vederas
Journal:  J Med Chem       Date:  2007-03-24       Impact factor: 7.446

5.  Scope and limitations of Pd2(dba)3/P(i-BuNCH2CH2)3N-catalyzed Buchwald-Hartwig amination reactions of aryl chlorides.

Authors:  Sameer Urgaonkar; John G Verkade
Journal:  J Org Chem       Date:  2004-12-24       Impact factor: 4.354

6.  Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems.

Authors:  G A Grasa; M S Viciu; J Huang; S P Nolan
Journal:  J Org Chem       Date:  2001-11-16       Impact factor: 4.354

7.  The first tandem double palladium-catalyzed aminations: synthesis of dipyrido[1,2-a:3',2'-d]imidazole and its benzo- and aza-analogues.

Authors:  Kristof T J Loones; Bert U W Maes; Roger A Dommisse; Guy L F Lemière
Journal:  Chem Commun (Camb)       Date:  2004-09-20       Impact factor: 6.222

8.  Synthesis and antioxidant activity evaluation of new 7-aryl or 7-heteroarylamino-2,3-dimethylbenzo[b]thiophenes obtained by Buchwald-Hartwig C-N cross-coupling.

Authors:  Maria-João R P Queiroz; Isabel C F R Ferreira; Ricardo C Calhelha; Letícia M Estevinho
Journal:  Bioorg Med Chem       Date:  2006-11-29       Impact factor: 3.641

9.  Synthesis of secondary arylamines through copper-mediated intermolecular aryl amination.

Authors:  Kentaro Okano; Hidetoshi Tokuyama; Tohru Fukuyama
Journal:  Org Lett       Date:  2003-12-25       Impact factor: 6.005

10.  Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles.

Authors:  Jon C Antilla; Jeremy M Baskin; Timothy E Barder; Stephen L Buchwald
Journal:  J Org Chem       Date:  2004-08-20       Impact factor: 4.354
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