Literature DB >> 20545315

Two-component approach toward a fully substituted N-fused pyrrole ring.

Dmitri Chernyak1, Cathy Skontos, Vladimir Gevorgyan.   

Abstract

An efficient two-component palladium-catalyzed arylation/cyclization cascade approach toward a variety of N-fused pyrroloheterocycles has been developed. This transformation proceeds via the palladium-catalyzed coupling of aryl halides with propargylic esters or ethers followed by the 5-endo-dig cyclization leading to highly functionalized pyrroloheterocycles in good to excellent yield.

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Year:  2010        PMID： 20545315      PMCID： PMC2908008          DOI： 10.1021/ol1011949

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


  22 in total

1.  Synthesis and functionalization of indoles through palladium-catalyzed reactions.

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Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

2.  Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

3.  Expeditious synthesis of highly substituted indolizinones via a palladium-catalyzed domino sequence.

Authors:  Ikyon Kim; Kyungsun Kim
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  A novel Cu-assisted cycloisomerization of alkynyl imines: efficient synthesis of pyrroles and pyrrole-containing heterocycles.

Authors:  A V Kel'in; A W Sromek; V Gevorgyan
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

5.  Molecular determinants of topoisomerase I poisoning by lamellarins: comparison with camptothecin and structure-activity relationships.

Authors:  Esther Marco; William Laine; Christelle Tardy; Amélie Lansiaux; Masatomo Iwao; Fumito Ishibashi; Christian Bailly; Federico Gago
Journal:  J Med Chem       Date:  2005-06-02       Impact factor: 7.446

6.  Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

7.  Molecular-targeted antitumor agents. 15. Neolamellarins from the marine sponge Dendrilla nigra inhibit hypoxia-inducible factor-1 activation and secreted vascular endothelial growth factor production in breast tumor cells.

Authors:  Rui Liu; Yang Liu; Yu-Dong Zhou; Dale G Nagle
Journal:  J Nat Prod       Date:  2007-10-25       Impact factor: 4.050

8.  Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

Authors:  Gilson Zeni; Richard C Larock
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

9.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

10.  Cross-coupling reactions of aryl pivalates with boronic acids.

Authors:  Kyle W Quasdorf; Xia Tian; Neil K Garg
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419
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  5 in total

1.  Palladium-catalyzed intramolecular carbopalladation/cyclization cascade: access to polycyclic N-fused heterocycles.

Authors:  Dmitri Chernyak; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2010-11-08       Impact factor: 6.005

2.  On the validity of Au-vinylidenes in the gold-catalyzed 1,2-migratory cycloisomerization of skipped propargylpyridines.

Authors:  Yuanzhi Xia; Alexander S Dudnik; Yahong Li; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2010-11-11       Impact factor: 6.005

3.  Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine.

Authors:  Natalia Chernyak; David Tilly; Zhou Li; Vladimir Gevorgyan
Journal:  ARKIVOC       Date:  2010-12-10       Impact factor: 1.140

4.  Palladium-catalyzed carbonylative cyclization/arylation cascade for 2-aroylindolizine synthesis.

Authors:  Zhou Li; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2012-11-28       Impact factor: 6.005

5.  Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines.

Authors:  V Helan; A V Gulevich; V Gevorgyan
Journal:  Chem Sci       Date:  2015-03       Impact factor: 9.825
  5 in total

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