Visible light-promoted tandem azidation/cyclization of N-arylenamines towards quinoxalines

Visible light-promoted tandem azidation/cyclization of N-arylenamines towards quinoxalines Journal of Photochemistry and Photobiology A: Chemistry 355 (2018) 382–388 Contents lists available at ScienceDirect Journal of Photochemistry and Photobiology A: Chemistry journal home page : www.elsevier.com/locat e/jphotochem Invited feature article Visible light-promoted tandem azidation/cyclization of N-arylenamines towards quinoxalines Dianjun Li, Haichao Ma, Ying Li*, Wei Yu* State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, PR China A R T I C L E I N F O A B S T R A C T Article history: Received 7 June 2017 This paper reports that N-arylenamines can be converted into quinoxalines via tandem azidation/ Received in revised form 17 July 2017 intramolecular CH amination under visible light irradiation by using 1-azidyl-1,2-benziodoxole as the Accepted 31 July 2017 azidating agent. The substituent was found to have a critical influence on the reaction, and thus different Available online 1 August 2017 conditions were required to fit the substrates of varied structural features. The conversion of N-aryl-3- arylenamine esters into the corresponding quinoxalines proceeded well under metal-free conditions, Keywords: whereas Cu(OAc) was required when N-aryl-3-trifluoromethyl enamine esters were used as the Azidation substrates. This method was also applied to the preparation of 2,3-diarylquinoxalines by using Ru CH http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Photochemistry and Photobiology A: Chemistry Elsevier

Visible light-promoted tandem azidation/cyclization of N-arylenamines towards quinoxalines

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Publisher
Elsevier
Copyright
Copyright © 2017 Elsevier B.V.
ISSN
1010-6030
eISSN
1873-2666
D.O.I.
10.1016/j.jphotochem.2017.07.043
Publisher site
See Article on Publisher Site

Abstract

Journal of Photochemistry and Photobiology A: Chemistry 355 (2018) 382–388 Contents lists available at ScienceDirect Journal of Photochemistry and Photobiology A: Chemistry journal home page : www.elsevier.com/locat e/jphotochem Invited feature article Visible light-promoted tandem azidation/cyclization of N-arylenamines towards quinoxalines Dianjun Li, Haichao Ma, Ying Li*, Wei Yu* State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, PR China A R T I C L E I N F O A B S T R A C T Article history: Received 7 June 2017 This paper reports that N-arylenamines can be converted into quinoxalines via tandem azidation/ Received in revised form 17 July 2017 intramolecular CH amination under visible light irradiation by using 1-azidyl-1,2-benziodoxole as the Accepted 31 July 2017 azidating agent. The substituent was found to have a critical influence on the reaction, and thus different Available online 1 August 2017 conditions were required to fit the substrates of varied structural features. The conversion of N-aryl-3- arylenamine esters into the corresponding quinoxalines proceeded well under metal-free conditions, Keywords: whereas Cu(OAc) was required when N-aryl-3-trifluoromethyl enamine esters were used as the Azidation substrates. This method was also applied to the preparation of 2,3-diarylquinoxalines by using Ru CH

Journal

Journal of Photochemistry and Photobiology A: ChemistryElsevier

Published: Mar 15, 2018

References

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