Literature DB >> 18465855

A simple, modular synthesis of substituted pyridines.

Songbai Liu1, Lanny S Liebeskind.   

Abstract

A simple, modular method to prepare highly substituted pyridines is disclosed. The method employs a cascade reaction comprising (1) a novel N-iminative, Cu-catalyzed cross-coupling of alkenylboronic acids at the N-O bond of alpha,beta-unsaturated ketoxime O-pentafluorobenzoates, (2) electrocyclization of the resulting 3-azatriene, and (3) air oxidation affording highly substituted pyridines in moderate to excellent isolated yields (43-91%). Starting materials are readily available, and functional group tolerance is very good.

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Year:  2008        PMID： 18465855      PMCID： PMC2664531          DOI： 10.1021/ja8013743

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  17 in total

1.  Significant acceleration of 6 pi-azaelectrocyclization resulting from a remarkable substituent effect and formal synthesis of the ocular age pigment A2-E by a new method for substituted pyridine synthesis.

Authors:  K Tanaka; H Mori; M Yamamoto; S Katsumura
Journal:  J Org Chem       Date:  2001-05-04       Impact factor: 4.354

2.  Torquoselective 6pi-electron electrocyclic ring closure of 1-azatrienes containing acyclic chirality at the C-terminus.

Authors:  Nadiya Sydorenko; Richard P Hsung; Eymi L Vera
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

3.  A new total synthesis of the zinc matrixmetalloproteinase inhibitor ageladine A featuring a biogenetically patterned 6pi-2-azatriene electrocyclization.

Authors:  Matthew L Meketa; Steven M Weinreb
Journal:  Org Lett       Date:  2007-01-30       Impact factor: 6.005

4.  Unusual Reactivity of (Vinylimino)phosphoranes and Their Utility in the Preparation of Pyridine and Dihydropyridine Derivatives.

Authors:  Pedro Molina; Aurelia Pastor; María Jesús Vilaplana
Journal:  J Org Chem       Date:  1996-11-15       Impact factor: 4.354

5.  Direct synthesis of pyridine derivatives.

Authors:  Mohammad Movassaghi; Matthew D Hill; Omar K Ahmad
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419

6.  Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts.

Authors:  Lunxiang Yin; Jürgen Liebscher
Journal:  Chem Rev       Date:  2007-01       Impact factor: 60.622

7.  Discovery of 4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido[2,3-d]pyrimidine, an orally active, non-nucleoside adenosine kinase inhibitor..

Authors:  C H Lee; M Jiang; M Cowart; G Gfesser; R Perner; K H Kim; Y G Gu; M Williams; M F Jarvis; E A Kowaluk; A O Stewart; S S Bhagwat
Journal:  J Med Chem       Date:  2001-06-21       Impact factor: 7.446

8.  Ab initio studies of

Authors: 
Journal:  J Org Chem       Date:  2000-04-21       Impact factor: 4.354

9.  Ruthenium-catalyzed cycloisomerization-6pi-cyclization: a novel route to pyridines.

Authors:  Barry M Trost; Alicia C Gutierrez
Journal:  Org Lett       Date:  2007-03-16       Impact factor: 6.005

10.  Stereoselective formal [3 + 3] cycloaddition approach to cis-1-azadecalins and synthesis of (-)-4a,8a-diepi-pumiliotoxin C. evidence for the first highly stereoselective 6pi-electron electrocyclic ring closures of 1-azatrienes.

Authors:  Heather M Sklenicka; Richard P Hsung; Michael J McLaughlin; Lin-Li Wei; Aleksey I Gerasyuto; William B Brennessel
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419
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  18 in total

1.  A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Shaolin Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-12       Impact factor: 15.336

Review 2.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

Review 3.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

4.  Transition State Gauche Effects Control the Torquoselectivities of the Electrocyclizations of Chiral 1-Azatrienes.

Authors:  Ashay Patel; Joseph R Vella; Zhi-Xiong Ma; R P Hsung; K N Houk
Journal:  J Org Chem       Date:  2015-10-16       Impact factor: 4.354

5.  Three-component coupling sequence for the regiospecific synthesis of substituted pyridines.

Authors:  Ming Z Chen; Glenn C Micalizio
Journal:  J Am Chem Soc       Date:  2011-12-14       Impact factor: 15.419

6.  Copper-catalyzed electrophilic amination of organolithiums mediated by recoverable siloxane transfer agents.

Authors:  Minh H Nguyen; Amos B Smith
Journal:  Org Lett       Date:  2013-09-03       Impact factor: 6.005

7.  An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols.

Authors:  Zhishi Ye; Mingji Dai
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.005

8.  Rh(III)-catalyzed regioselective synthesis of pyridines from alkenes and α,β-unsaturated oxime esters.

Authors:  Jamie M Neely; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-12-18       Impact factor: 15.419

9.  N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with o-acetyl hydroxamic acids.

Authors:  Zhihui Zhang; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2008-06-17       Impact factor: 6.005

10.  A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction.

Authors:  Christian Eidamshaus; Roopender Kumar; Mrinal K Bera; Hans-Ulrich Reissig
Journal:  Beilstein J Org Chem       Date:  2011-07-13       Impact factor: 2.883
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