Scope of Tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the Synthesis of  Triazoloquinoxalines,  Imidazoloquinoxalines, and Rhenium-complexes thereof

  1. Laura HolzhauerORCID Logo,
  2. Chloé Liagre,
  3. Olaf FuhrORCID Logo,
  4. Nicole JungORCID Logo and
  5. Stefan BräseORCID Logo

Submitting author affiliation: Karlsruher Institut für Technologie, Eggenstein-Leopoldshafen, Germany

Beilstein Arch. 2022, 202210. https://doi.org/10.3762/bxiv.2022.10.v1

Published 28 Feb 2022

  • Preprint

Abstract

The conversion of tetrazolo[1,5-a]quinoxalines to 1,2,3-triazoloquinoxalines and triazoloimidazoquinoxalines under typical conditions of a CuAAC reaction has been investigated. Derivatives of the novel compound class of triazoloimidazoquinoxalines (TIQ) and rhenium(I) triazoloquinoxaline complexes as well as a new TIQ rhenium complex were synthesized. As a result, a small 1,2,3-triazoloquinoxaline library was obtained and the method could be expanded towards 4-substituted tetrazoloquinoxalines. The compatibility of various aliphatic and aromatic alkynes towards the reaction was investigated and the denitrogenative annulation towards imidazoloquinoxalines could be observed as a competing reaction depending on the alkyne concentration and the substitutions at the quinoxaline.

Keywords: Quinoxaline, Tetrazole, Triazole, Imidazole, Click Reaction, CuAAC, Denitrogenative Annulation, Metal Complexes

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Holzhauer, L.; Liagre, C.; Fuhr, O.; Jung, N.; Bräse, S. Beilstein Arch. 2022, 202210. doi:10.3762/bxiv.2022.10.v1

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