Literature DB >> 17309277

Pt-catalyzed cyclization/1,2-migration for the synthesis of indolizines, pyrrolones, and indolizinones.

Cameron R Smith1, Eric M Bunnelle, Allison J Rhodes, Richmond Sarpong.   

Abstract

Indolizine, pyrrolone, and indolizinone heterocycles are easily accessed via the Pt(II)-catalyzed cycloisomerization or a tandem cyclization/1,2-migration of pyridine propargylic alcohols and derivatives. This method provides an efficient synthesis of highly functionalized heterocycles from readily available substrates. [reaction: see text]

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Year:  2007        PMID： 17309277      PMCID： PMC3384527          DOI： 10.1021/ol0701971

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


  13 in total

1.  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

2.  Gold(III)- and platinum(II)-catalyzed domino reaction consisting of heterocyclization and 1,2-migration: efficient synthesis of highly substituted 3(2H)-furanones.

Authors:  Stefan F Kirsch; Jörg T Binder; Clémence Liébert; Helge Menz
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-04       Impact factor: 15.336

3.  An improved synthesis of functionalized biphenyl-based phosphine ligands.

Authors:  H Tomori; J M Fox; S L Buchwald
Journal:  J Org Chem       Date:  2000-08-25       Impact factor: 4.354

4.  Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.

Authors:  B A Bhanu Prasad; Francis K Yoshimoto; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2005-09-14       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.  Platinum-catalyzed intramolecular hydroamination of unactivated olefins with secondary alkylamines.

Authors:  Christopher F Bender; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

7.  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

8.  PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.

Authors:  Youssef Harrak; Christophe Blaszykowski; Matthieu Bernard; Kevin Cariou; Emily Mainetti; Virginie Mouriès; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

9.  Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes.

Authors:  Victor Mamane; Tobias Gress; Helga Krause; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

10.  Ruthenium-catalyzed cyclopropanation of alkenes using propargylic carboxylates as precursors of vinylcarbenoids.

Authors:  Koji Miki; Kouichi Ohe; Sakae Uemura
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354
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  23 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.  Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones.

Authors:  Eric M Bunnelle; Cameron R Smith; Sharon K Lee; Surendra W Singaram; Allison J Rhodes; Richmond Sarpong
Journal:  Tetrahedron       Date:  2008-02-28       Impact factor: 2.457

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

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2007-07-17       Impact factor: 6.005

4.  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

5.  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

6.  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

7.  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

8.  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

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.  (7R,8S,8aS)-8-Hydr-oxy-7-phenyl-perhydro-indolizin-3-one.

Authors:  Lubomír Svorc; Viktor Vrábel; Stefan Marchalín; Peter Safář; Jozef Kožíšek
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-23
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