Literature DB >> 20518526

Synthesis of multicyclic pyridine and quinoline derivatives via intramolecular C-H bond functionalization.

Sirilata Yotphan1, Robert G Bergman, Jonathan A Ellman.   

Abstract

An efficient method is reported for the preparation of multicyclic pyridines and quinolines by a rhodium-catalyzed intramolecular C-H bond functionalization process. The method shows good scope for branched and unbranched alkyl substituents on the pyridine ring and at the R position of the tethered alkene group. Starting materials capable of undergoing olefin isomerization to provide terminal 1,1-disubstituted alkenes also proved to be effective substrates.

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Year:  2010        PMID: 20518526      PMCID: PMC2892546          DOI: 10.1021/ol101002b

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


  28 in total

1.  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

2.  Synthesis of potent bicyclic bisarylimidazole c-Jun N-terminal kinase inhibitors by catalytic C-H bond activation.

Authors:  Jason C Rech; Michihisa Yato; Derek Duckett; Brian Ember; Philip V LoGrasso; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2007-01-24       Impact factor: 15.419

3.  A strategy for C-H activation of pyridines: direct C-2 selective alkenylation of pyridines by nickel/Lewis acid catalysis.

Authors:  Yoshiaki Nakao; Kyalo Stephen Kanyiva; Tamejiro Hiyama
Journal:  J Am Chem Soc       Date:  2008-02-05       Impact factor: 15.419

4.  Selective preparation of pyridines, pyridones, and iminopyridines from two different alkynes via azazirconacycles.

Authors:  Tamotsu Takahashi; Fu-Yu Tsai; Yanzhong Li; Hui Wang; Yoshihiko Kondo; Masamichi Yamanaka; Kiyohiko Nakajima; Martin Kotora
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

5.  Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

Authors:  Dipannita Kalyani; Nicholas R Deprez; Lopa V Desai; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

6.  Pd0/PR3-catalyzed arylation of nicotinic and isonicotinic acid derivatives.

Authors:  Masayuki Wasa; Brady T Worrell; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-08       Impact factor: 15.336

7.  The discovery of thienopyridine analogues as potent IkappaB kinase beta inhibitors. Part II.

Authors:  Jiang-Ping Wu; Roman Fleck; Janice Brickwood; Alison Capolino; Katrina Catron; Zhidong Chen; Charles Cywin; Jonathan Emeigh; Melissa Foerst; John Ginn; Matt Hrapchak; Eugene Hickey; Ming-Hong Hao; Mohammed Kashem; Jun Li; Weimin Liu; Tina Morwick; Richard Nelson; Daniel Marshall; Leslie Martin; Peter Nemoto; Ian Potocki; Michel Liuzzi; Gregory W Peet; Erika Scouten; David Stefany; Michael Turner; Steve Weldon; Clare Zimmitti; Denise Spero; Terence A Kelly
Journal:  Bioorg Med Chem Lett       Date:  2009-08-15       Impact factor: 2.823

8.  Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.

Authors:  Alexandre Larivée; James J Mousseau; André B Charette
Journal:  J Am Chem Soc       Date:  2007-12-08       Impact factor: 15.419

9.  N3-arylmalonamides: a new series of thieno[3,2-b]pyridine based inhibitors of c-Met and VEGFR2 tyrosine kinases.

Authors:  Oscar Saavedra; Stephen Claridge; Lijie Zhan; Franck Raeppel; Marie-Claude Granger; Stéphane Raeppel; Michael Mannion; Frédéric Gaudette; Nancy Zhou; Ljubomir Isakovic; Naomy Bernstein; Robert Déziel; Hannah Nguyen; Normand Beaulieu; Carole Beaulieu; Isabelle Dupont; James Wang; A Robert Macleod; Jeffrey M Besterman; Arkadii Vaisburg
Journal:  Bioorg Med Chem Lett       Date:  2009-10-25       Impact factor: 2.823

10.  2-Alkenylthieno[2,3-b]pyridine-5-carbonitriles: Potent and selective inhibitors of PKCtheta.

Authors:  L Nathan Tumey; Diane H Boschelli; Julie Lee; Divya Chaudhary
Journal:  Bioorg Med Chem Lett       Date:  2008-06-18       Impact factor: 2.823

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  2 in total

1.  Rh(I)-catalyzed direct arylation of azines.

Authors:  Ashley M Berman; Robert G Bergman; Jonathan A Ellman
Journal:  J Org Chem       Date:  2010-10-29       Impact factor: 4.354

Review 2.  Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage.

Authors:  Gagandeep Kour Reen; Ashok Kumar; Pratibha Sharma
Journal:  Beilstein J Org Chem       Date:  2019-07-19       Impact factor: 2.883

  2 in total

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