Literature DB >> 24093728

Intramolecular transannulation of alkynyl triazoles via alkyne-carbene metathesis step: access to fused pyrroles.

Yi Shi1, Vladimir Gevorgyan.   

Abstract

An intramolecular Rh-catalyzed transannulation reaction of alkynyl triazoles has been developed. This method allows efficient construction of various 5,5-fused pyrroles, including tetrahydropyrrolo and spiro systems. The method demonstrates excellent functional group compatibility. A rhodium carbene-alkyne metathesis mechanism is proposed for this transformation.

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Year:  2013        PMID： 24093728      PMCID： PMC3946541          DOI： 10.1021/ol4027655

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


  24 in total

Review 1.  Transition-metal-catalyzed denitrogenative transannulation: converting triazoles into other heterocyclic systems.

Authors:  Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-25       Impact factor: 15.336

2.  Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles.

Authors:  Stepan Chuprakov; Frank W Hwang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: controlling selectivity.

Authors:  Eun Jeong Yoo; Mårten Ahlquist; Seok Hwan Kim; Imhyuck Bae; Valery V Fokin; K Barry Sharpless; Sukbok Chang
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  1,3-Diaryl-4,5,6,7-tetrahydro-2H-isoindole derivatives: a new series of potent and selective COX-2 inhibitors in which a sulfonyl group is not a structural requisite.

Authors:  B Portevin; C Tordjman; P Pastoureau; J Bonnet
Journal:  J Med Chem       Date:  2000-11-30       Impact factor: 7.446

5.  Versatile reactivity of rhodium-iminocarbenes derived from N-sulfonyl triazoles.

Authors:  Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-07       Impact factor: 15.336

6.  Palladium-catalyzed mono-α-arylation of acetone with aryl halides and tosylates.

Authors:  Kevin D Hesp; Rylan J Lundgren; Mark Stradiotto
Journal:  J Am Chem Soc       Date:  2011-03-18       Impact factor: 15.419

7.  Highly regioselective palladium-catalyzed direct arylation of oxazole at C-2 or C-5 with aryl bromides, chlorides, and triflates.

Authors:  Neil A Strotman; Harry R Chobanian; Yan Guo; Jiafang He; Jonathan E Wilson
Journal:  Org Lett       Date:  2010-08-20       Impact factor: 6.005

8.  Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles.

Authors:  Tony Horneff; Stepan Chuprakov; Natalia Chernyak; Vladimir Gevorgyan; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

9.  Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.

Authors:  Stepan Chuprakov; Sen Wai Kwok; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-03-15       Impact factor: 15.419

10.  Synthesis of enaminones by rhodium-catalyzed denitrogenative rearrangement of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols.

Authors:  Tomoya Miura; Yuuta Funakoshi; Masao Morimoto; Tsuneaki Biyajima; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2012-10-15       Impact factor: 15.419
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  7 in total

1.  A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

Authors:  Alexey Kuznetsov; Anton V Gulevich; Donald J Wink; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-01       Impact factor: 15.336

2.  Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.

Authors:  Yi Shi; Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-21       Impact factor: 15.336

3.  Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles.

Authors:  Erica E Schultz; Vincent N G Lindsay; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-15       Impact factor: 15.336

4.  Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

Authors:  Liangbing Fu; Huw M L Davies
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

5.  Light-induced metal-free transformations of unactivated pyridotriazoles.

Authors:  Ziyan Zhang; Dongari Yadagiri; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2019-07-25       Impact factor: 9.825

6.  Synthesis of 2,5-diaryloxazoles through rhodium-catalyzed annulation of triazoles and aldehydes.

Authors:  Jian Li; Shang-Rong Zhu; Yue Xu; Xue-Chen Lu; Zheng-Bing Wang; Li Liu; De-Feng Xu
Journal:  RSC Adv       Date:  2020-06-30       Impact factor: 4.036

7.  Tandem 1,2-sulfur migration and (aza)-Diels-Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes.

Authors:  Dongari Yadagiri; Pazhamalai Anbarasan
Journal:  Chem Sci       Date:  2015-07-10       Impact factor: 9.825
  7 in total

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