Literature DB >> 17637023

Base- and ligand-free room-temperature synthesis of N-fused heteroaromatic compounds via the transition metal-catalyzed cycloisomerization protocol.

Ilya V Seregin1, Alex W Schammel, Vladimir Gevorgyan.   

Abstract

A new practical method for the synthesis of N-fused heterocycles via the transition metal-catalyzed cycloisomerization of heterocyles possessing a propagyl group has been developed. This very mild, base- and ligand-free method allows for the synthesis of diverse fused heterocyclic cores in good to excellent yields.

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Year:  2007        PMID： 17637023      PMCID： PMC2525811          DOI： 10.1021/ol701464j

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


  21 in total

1.  Silver-catalyzed hydroamination of siloxy alkynes.

Authors:  Jianwei Sun; Sergey A Kozmin
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-24       Impact factor: 15.336

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.  Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-03-20       Impact factor: 15.419

4.  Direct palladium-catalyzed alkynylation of N-fused heterocycles.

Authors:  Ilya V Seregin; Victoria Ryabova; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

5.  Direct synthesis of monofunctionalized indolizine derivatives bearing alkoxymethyl substituents at C-3 and their benzofused analogues.

Authors:  Joseph Kaloko; Anthony Hayford
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

6.  Synthesis of indenyl ethers by gold(I)-catalyzed intramolecular carboalkoxylation of alkynes.

Authors:  Pascal Dubé; F Dean Toste
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

7.  Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols.

Authors:  Volker Belting; Norbert Krause
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

8.  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

9.  Gold catalysis: mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects.

Authors:  A Stephen K Hashmi; Jan P Weyrauch; Wolfgang Frey; Jan W Bats
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

10.  Potent inhibitors of secretory phospholipase A2: synthesis and inhibitory activities of indolizine and indene derivatives.

Authors:  S Hagishita; M Yamada; K Shirahase; T Okada; Y Murakami; Y Ito; T Matsuura; M Wada; T Kato; M Ueno; Y Chikazawa; K Yamada; T Ono; I Teshirogi; M Ohtani
Journal:  J Med Chem       Date:  1996-09-13       Impact factor: 7.446
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  14 in total

1.  Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information.

Authors:  Alison R Hardin Narayan; Richmond Sarpong
Journal:  Org Biomol Chem       Date:  2011-11-09       Impact factor: 3.876

2.  Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles.

Authors:  Dmitri Chernyak; Surendra Babu Gadamsetty; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2008-05-08       Impact factor: 6.005

3.  One-pot synthesis of highly substituted N-fused heteroaromatic bicycles from azole aldehydes.

Authors:  Victor K Outlaw; Felipe B d'Andrea; Craig A Townsend
Journal:  Org Lett       Date:  2015-03-27       Impact factor: 6.005

4.  ORGANOCOPPER-MEDIATED TWO-COMPONENT SN2'-SUBSTITUTION CASCADE TOWARDS N-FUSED HETEROCYCLES.

Authors:  D Chernyak; V Gevorgyan
Journal:  Chem Heterocycl Compd (N Y)       Date:  2012-03-01       Impact factor: 1.277

5.  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

6.  Remarkable facilitation of hetero-cycloisomerizations with water and other polar protic solvents: metal-free synthesis of indolizines.

Authors:  Alison R Hardin Narayan; Richmond Sarpong
Journal:  Green Chem       Date:  2010       Impact factor: 10.182

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

Authors:  Dmitri Chernyak; Cathy Skontos; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2010-07-16       Impact factor: 6.005

8.  Protic-solvent-mediated cycloisomerization of quinoline and isoquinoline propargylic alcohols: syntheses of (±)-3-demethoxyerythratidinone and (±)-cocculidine.

Authors:  Stephen T Heller; Toshihiro Kiho; Alison R H Narayan; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-05       Impact factor: 15.336

9.  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

10.  Reactivity of diphenylpropynone derivatives toward metal-associated amyloid-β species.

Authors:  Amit S Pithadia; Akiko Kochi; Molly T Soper; Michael W Beck; Yuzhong Liu; Sanghyun Lee; Alaina S DeToma; Brandon T Ruotolo; Mi Hee Lim
Journal:  Inorg Chem       Date:  2012-11-15       Impact factor: 5.165
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