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Literature DB >> 23477345

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

Stepan Chuprakov¹, Sen Wai Kwok, Valery V Fokin.

Abstract

Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazole-diazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle.

Entities: Chemical Disease Gene Species

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Year: 2013 PMID： 23477345 PMCID： PMC3645925 DOI： 10.1021/ja400350c

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

23 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. 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

5. Synthesis and reactivity of rhodium(II) N-triflyl azavinyl carbenes.

Authors: Neil Grimster; Li Zhang; Valery V Fokin
Journal: J Am Chem Soc Date: 2010-03-03 Impact factor: 15.419

6. N-H insertion reactions of primary ureas: the synthesis of highly substituted imidazolones and imidazoles from diazocarbonyls.

Authors: Sang-Hyeup Lee; Kazuhiro Yoshida; Hana Matsushita; Bruce Clapham; Guido Koch; Jürg Zimmermann; Kim D Janda
Journal: J Org Chem Date: 2004-12-10 Impact factor: 4.354

7. 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

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. 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

10. Arylation of rhodium(II) azavinyl carbenes with boronic acids.

Authors: Nicklas Selander; Brady T Worrell; Stepan Chuprakov; Subash Velaparthi; Valery V Fokin
Journal: J Am Chem Soc Date: 2012-08-28 Impact factor: 15.419

15 in total

1. Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

Authors: Sen Wai Kwok; Li Zhang; Neil P Grimster; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2014-03-24 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. 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

4. Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.

Authors: Hillary J Dequina; Jennifer M Schomaker
Journal: Trends Chem Date: 2020-09-02

5. 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

6. 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

7. Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: synthesis of 4-haloisoxazoles and 5-halotriazoles.

Authors: James S Oakdale; Rakesh K Sit; Valery V Fokin
Journal: Chemistry Date: 2014-07-24 Impact factor: 5.236