Literature DB >> 25682847

Rh(II)-catalyzed cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines: switchable reactivity of Rh-azavinylcarbene as [2C]- or aza-[3C]-synthon.

Yuanhao Wang1, Xiaoqiang Lei, Yefeng Tang.   

Abstract

The Rh(II)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions.

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Year:  2015        PMID: 25682847     DOI: 10.1039/c5cc00268k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  8 in total

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Journal:  Organometallics       Date:  2018-09-10       Impact factor: 3.876

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Journal:  Angew Chem Int Ed Engl       Date:  2018-05-14       Impact factor: 15.336

3.  Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds.

Authors:  Pavel A Sakharov; Nikolai V Rostovskii; Alexander F Khlebnikov; Mikhail S Novikov
Journal:  Molecules       Date:  2022-09-02       Impact factor: 4.927

4.  Regiodivergent synthesis of pyrazino-indolines vs. triazocines via α-imino carbenes addition to imidazolidines.

Authors:  Alejandro Guarnieri-Ibáñez; Adiran de Aguirre; Céline Besnard; Amalia I Poblador-Bahamonde; Jérôme Lacour
Journal:  Chem Sci       Date:  2020-11-23       Impact factor: 9.825

5.  Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids.

Authors:  Yuanhao Wang; Yunfei Wu; Yuanhe Li; Yefeng Tang
Journal:  Chem Sci       Date:  2017-03-15       Impact factor: 9.825

6.  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.  Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from N-sulfonyl-1,2,3-triazoles and ortho-vinylanilines.

Authors:  Dongari Yadagiri; Angula Chandra Shekar Reddy; Pazhamalai Anbarasan
Journal:  Chem Sci       Date:  2016-05-24       Impact factor: 9.825

8.  Chemical Consequences of the Mechanical Bond: A Tandem Active Template-Rearrangement Reaction.

Authors:  Florian Modicom; Ellen M G Jamieson; Elise Rochette; Stephen M Goldup
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-14       Impact factor: 15.336

  8 in total

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