Synthesis 2020; 52(23): 3564-3576
DOI: 10.1055/s-0040-1707254
short review

Recent Advances in Denitrogenative Reactions of Pyridotriazoles

Ilya P. Filippov
,
Gleb D. Titov
,
Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg 199034, Russian Federation   Email: [email protected]
› Author Affiliations
This work was supported by a research grant from the Russian Science Foundation (Grant No. 19-73-10090).


Dedicated to Prof. Mikhail S. Novikov on the occasion of his 60th birthday and to Prof. Alexander F. Khlebnikov on the occasion of his 70th birthday

Abstract

Diazo compounds display versatile reactivity and therefore are widely used in organic synthesis. Diazo compounds bearing a 2-pyridyl or a related azine moiety on the diazo carbon exist in the form of fused 1,2,3-triazoles. In this short review, we summarize the recent advances in denitrogenative reactions of [1,2,3]triazolo[1,5-a]pyridines (‘pyridotriazoles’) and related fused 1,2,3-triazoles. Over the past decade, there has been a surge of activity in this field, with novel denitrogenative reactions of pyridotriazoles induced by metal compounds, light, and Brønsted and Lewis acids having been devised. As a result, heterocyclic compounds and functionalized α-picolines as well as bio­active molecules have been synthesized. In the review, emphasis is also placed on the mechanisms of the new reactions.

1 Introduction

2 Ring-Chain Isomerization of Pyridotriazoles

3 Metal-Catalyzed Reactions

3.1 Rh(II) Catalysis

3.2 Rh(III) Catalysis

3.3 Cu Catalysis

3.4 Pd Catalysis

3.5 Catalysis by Other Metals

4 Metal-Free Reactions

5 Conclusion



Publication History

Received: 03 June 2020

Accepted after revision: 24 July 2020

Publication Date:
25 August 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
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