Literature DB >> 22121072

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

Buddhadeb Chattopadhyay1, Vladimir Gevorgyan.   

Abstract

Transition metal catalyzed denitrogenative transannulation of a triazole ring has recently received considerable attention as a new concept for the construction of diverse nitrogen-containing heterocyclic cores. This method allows a single-step synthesis of complex nitrogen heterocycles from easily available and cheap triazole precursors. In this Minireview, recent progress of the transition metal catalyzed denitrogenative transannulation of a triazole ring, which was discovered in 2007, is discussed.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID: 22121072      PMCID: PMC3393755          DOI: 10.1002/anie.201104807

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  47 in total

1.  Recent Advances in Asymmetric Catalytic Metal Carbene Transformations.

Authors:  Michael P. Doyle; David C. Forbes
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

2.  Inhibitors of HIV-1 protease by using in situ click chemistry.

Authors:  Matthew Whiting; John Muldoon; Ying-Chuan Lin; Steven M Silverman; William Lindstrom; Arthur J Olson; Hartmuth C Kolb; M G Finn; K Barry Sharpless; John H Elder; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-20       Impact factor: 15.336

3.  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

4.  Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles.

Authors:  Bantwal Shivarama Holla; Manjathuru Mahalinga; Mari Sithambaram Karthikeyan; Boja Poojary; Padiyath Mohammed Akberali; Nalilu Suchetha Kumari
Journal:  Eur J Med Chem       Date:  2005-06-24       Impact factor: 6.514

5.  Nickel-catalyzed denitrogenative annulation reactions of 1,2,3-benzotriazin-4(3H)-ones with 1,3-dienes and alkenes.

Authors:  Tomoya Miura; Masao Morimoto; Motoshi Yamauchi; Masahiro Murakami
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

6.  Highly efficient synthesis of isoquinolines via nickel-catalyzed annulation of 2-iodobenzaldimines with alkynes: evidence for dual pathways of alkyne insertion.

Authors:  Rajendra Prasad Korivi; Chien-Hong Cheng
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

Review 7.  Pyranose N-glycosyl amines: emerging targets with diverse biological potential.

Authors:  Peter Norris
Journal:  Curr Top Med Chem       Date:  2008       Impact factor: 3.295

8.  Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles.

Authors:  Tomoya Miura; Motoshi Yamauchi; Masahiro Murakami
Journal:  Chem Commun (Camb)       Date:  2009-01-06       Impact factor: 6.222

9.  Design, synthesis, and structure-activity relationship of substrate competitive, selective, and in vivo active triazole and thiadiazole inhibitors of the c-Jun N-terminal kinase.

Authors:  Surya K De; John L Stebbins; Li-Hsing Chen; Megan Riel-Mehan; Thomas Machleidt; Russell Dahl; Hongbin Yuan; Aras Emdadi; Elisa Barile; Vida Chen; Ria Murphy; Maurizio Pellecchia
Journal:  J Med Chem       Date:  2009-04-09       Impact factor: 7.446

10.  Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides.

Authors:  Brendan L Wilkinson; Laurent F Bornaghi; Todd A Houston; Alessio Innocenti; Daniela Vullo; Claudiu T Supuran; Sally-Ann Poulsen
Journal:  J Med Chem       Date:  2007-03-08       Impact factor: 7.446

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  25 in total

1.  Highly enantioselective dearomatizing formal [3+3] cycloaddition reactions of N-acyliminopyridinium ylides with electrophilic enol carbene intermediates.

Authors:  Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

2.  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

3.  N-2-Aryl-1,2,3-Triazoles: A Novel Class of Blue Emitting Fluorophores-Synthesis, Photophysical Properties Study and DFT Computations.

Authors:  Vikas S Padalkar; Sandip K Lanke; Santosh B Chemate; Nagaiyan Sekar
Journal:  J Fluoresc       Date:  2015-05-15       Impact factor: 2.217

Review 4.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

5.  Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines.

Authors:  John M Bennett; Jonathan D Shapiro; Krystina N Choinski; Yingbin Mei; Sky M Aulita; Giovanny M Dominguez; Max M Majireck
Journal:  J Vis Exp       Date:  2018-01-03       Impact factor: 1.355

6.  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

7.  Ring expansion and rearrangements of rhodium(II) azavinyl carbenes.

Authors:  Nicklas Selander; Brady T Worrell; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-19       Impact factor: 15.336

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

Authors:  Yi Shi; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2013-10-04       Impact factor: 6.005

9.  Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes.

Authors:  Stepan Chuprakov; Brady T Worrell; Nicklas Selander; Rakesh K Sit; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

10.  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

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