Literature DB >> 23777199

Regiocontrolled synthesis of polysubstituted pyrroles starting from terminal alkynes, sulfonyl azides, and allenes.

Tomoya Miura1, Kentaro Hiraga, Tsuneaki Biyajima, Takayuki Nakamuro, Masahiro Murakami.   

Abstract

1-Sulfonyl-1,2,3-triazoles, readily prepared from terminal alkynes and sulfonyl azides, react with allenes in the presence of a nickel(0) catalyst to produce the corresponding isopyrroles. The initially produced isopyrroles are further converted to a wide range of polysubstituted pyrroles through double bond transposition and Alder-ene reactions.

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Year:  2013        PMID： 23777199     DOI： 10.1021/ol401340u

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


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

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

5.  Rh-Catalyzed Aziridine Ring Expansions to Dehydropiperazines.

Authors:  Hillary J Dequina; Josephine Eshon; William T Raskopf; Israel Fernández; Jennifer M Schomaker
Journal:  Org Lett       Date:  2020-04-22       Impact factor: 6.005

6.  Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines.

Authors:  V Helan; A V Gulevich; V Gevorgyan
Journal:  Chem Sci       Date:  2015-03       Impact factor: 9.825

7.  Copper(I)-catalyzed multicomponent reaction providing a new access to fully substituted thiophene derivatives.

Authors:  Bo Jiang; Xing-Jun Tu; Xue Wang; Shu-Jiang Tu; Guigen Li
Journal:  Org Lett       Date:  2014-07-02       Impact factor: 6.005

8.  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

9.  Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes.

Authors:  Olga Bakhanovich; Viktor Khutorianskyi; Vladimir Motornov; Petr Beier
Journal:  Beilstein J Org Chem       Date:  2021-02-18       Impact factor: 2.883

10.  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
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