Literature DB >> 24660875

Synthesis of pyrroles from terminal alkynes, N-sulfonyl azides, and alkenyl alkyl ethers through 1-sulfonyl-1,2,3-triazoles.

Cheol-Eui Kim1, Sangjune Park, Dahan Eom, Boram Seo, Phil Ho Lee.   

Abstract

A method for synthesis of substituted pyrroles has been developed. 1-Sulfonyl-1,2,3-triazoles generated from terminal alkynes gave α-imino rhodium carbene complexes, which when reacted with alkenyl alkyl ethers afforded substituted pyrroles. The method can be efficiently applied to a one-pot sequential reaction starting from terminal alkynes.

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Year:  2014        PMID： 24660875     DOI： 10.1021/ol500718s

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


  8 in total

1.  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

2.  Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities.

Authors:  John T Gupton; Scott Yeudall; Nakul Telang; Megan Hoerrner; Ellis Huff; Evan Crawford; Katie Lounsbury; Michael Kimmel; William Curry; Andrew Harrison; Wen Juekun; Alex Shimozono; Joe Ortolani; Kristin Lescalleet; Jon Patteson; Veronica Moore-Stoll; Cristina C Rohena; Susan L Mooberry; Ahmad J Obaidullah; Glen E Kellogg; James A Sikorski
Journal:  Bioorg Med Chem       Date:  2017-04-11       Impact factor: 3.641

3.  Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles.

Authors:  John T Gupton; Alex Shimozono; Evan Crawford; Joe Ortolani; Evan Clark; Matt Mahoney; Campbell Heese; Jeffrey Noble; Carlos Perez Mandry; Rene Kanters; Raymond N Dominey; Emma W Goldman; James A Sikorski; Daniel C Fisher
Journal:  Tetrahedron       Date:  2018-04-07       Impact factor: 2.457

4.  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

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 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

7.  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

8.  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
  8 in total

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