Literature DB >> 17362020

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

Barry M Trost1, Alicia C Gutierrez.   

Abstract

[reaction: see text] Herein we report a method for the synthesis of substituted pyridines. The unsaturated ketones and aldehydes derived from the cycloisomerization of primary and secondary propargyl diynols in the presence of [CpRu(CH3CN)3]PF6 (1) are converted to 1-azatrienes which in turn undergo a subsequent electrocyclization-dehydration to provide pyridines with excellent regiocontrol.

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Year:  2007        PMID： 17362020      PMCID： PMC2678947          DOI： 10.1021/ol070163t

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


  7 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.  Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition.

Authors:  Jesús A Varela; Carlos Saá
Journal:  Chem Rev       Date:  2003-09       Impact factor: 60.622

3.  Ruthenium-catalyzed cycloaddition of 1,6-diynes and nitriles under mild conditions: role of the coordinating group of nitriles.

Authors:  Yoshihiko Yamamoto; Keisuke Kinpara; Ryuji Ogawa; Hisao Nishiyama; Kenji Itoh
Journal:  Chemistry       Date:  2006-07-17       Impact factor: 5.236

4.  A nickel-catalyzed route to pyridines.

Authors:  Michael M McCormick; Hung A Duong; Gang Zuo; Janis Louie
Journal:  J Am Chem Soc       Date:  2005-04-13       Impact factor: 15.419

5.  Ruthenium-catalyzed cycloisomerizations of diynols.

Authors:  Barry M Trost; Michael T Rudd
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

6.  Synthesis of substituted pyridine derivatives via the ruthenium-catalyzed cycloisomerization of 3-azadienynes.

Authors:  Mohammad Movassaghi; Matthew D Hill
Journal:  J Am Chem Soc       Date:  2006-04-12       Impact factor: 15.419

7.  An unusual ruthenium-catalyzed cycloisomerization of alkynes and propargyl alcohols.

Authors:  Barry M Trost; Michael T Rudd
Journal:  J Am Chem Soc       Date:  2002-04-24       Impact factor: 15.419
  7 in total
  14 in total

1.  Synthesis of dihydropyridines and pyridines from imines and alkynes via C-H activation.

Authors:  Denise A Colby; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

Review 2.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

3.  Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cp(t) provide complementary selectivity.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  Chem Commun (Camb)       Date:  2011-10-10       Impact factor: 6.222

4.  Design and development of FGF-23 antagonists: Definition of the pharmacophore and initial structure-activity relationships probed by synthetic analogues.

Authors:  Ryan P Downs; Zhousheng Xiao; Munachi O Ikedionwu; Jacob W Cleveland; Ai Lin Chin; Abigail E Cafferty; L Darryl Quarles; Jesse D Carrick
Journal:  Bioorg Med Chem       Date:  2020-11-18       Impact factor: 3.641

5.  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

6.  Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors:  Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

7.  One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles.

Authors:  James R Manning; Huw M L Davies
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419

8.  Synthesis of pyridines from ketoximes and terminal alkynes via C-H bond functionalization.

Authors:  Rhia M Martin; Robert G Bergman; Jonathan A Ellman
Journal:  J Org Chem       Date:  2012-02-14       Impact factor: 4.354

9.  A simple, modular synthesis of substituted pyridines.

Authors:  Songbai Liu; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2008-05-09       Impact factor: 15.419

10.  Diversity synthesis of complex pyridines yields a probe of a neurotrophic signaling pathway.

Authors:  B Lawrence Gray; Xiang Wang; W Colby Brown; Letian Kuai; Stuart L Schreiber
Journal:  Org Lett       Date:  2008-05-30       Impact factor: 6.005
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