Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

  1. Soumyaranjan PatiORCID Logo,
  2. Renata G. AlmeidaORCID Logo,
  3. Eufrânio N. da Silva JúniorORCID Logo and
  4. Irishi N. N. NamboothiriORCID Logo

Submitting author affiliation: IIT Bombay, Mumbai, India

Beilstein Arch. 2020, 2020134. https://doi.org/10.3762/bxiv.2020.134.v1

Published 27 Nov 2020

  • Preprint

Abstract

Desulfonylative alkylation of N-tosyl-1,2,3-triazoles under metal-free conditions leading to β-triazolylenones is reported here. The present study encompasses the synthesis of triazoles with a new substitution pattern in a single step from cyclic 1,3-dicarbonyl compounds and N-tosyl triazole in moderate to high yields. Our synthesis takes place with complete regioselectivity as confirmed by crystallographic analysis which is rationalized by suitable mechanistic proposal. This method provides an efficient, versatile and straightforward strategy towards the synthesis of new 1,2,3-triazoles.

Keywords: 1,2,3-triazoles; enones; cycloaddition; heterocycles; azoles.

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Pati, S.; Almeida, R. G.; da Silva Júnior, E. N.; Namboothiri, I. N. N. Beilstein Arch. 2020, 2020134. doi:10.3762/bxiv.2020.134.v1

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