Dedicated to Prof. Mikhail S. Novikov on the occasion of his 60^th birthday and to Prof. Alexander F. Khlebnikov on the occasion of his 70^th 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
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

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吡啶三唑脱氮反应的最新进展

专用于米哈伊尔·诺维科夫S.教授在他的60之际^个生日，亚历山大教授F. Khlebnikov在他70之际^个生日

抽象

重氮化合物显示出多种反应性，因此被广泛用于有机合成中。在重氮碳上带有2-吡啶基或相关的嗪部分的重氮化合物以稠合的1,2,3-三唑的形式存在。在这篇简短的评论中，我们总结了[1,2,3]三唑并[1,5- a ]吡啶（“吡啶三唑”）和相关稠合的1,2,3-三唑的脱氮反应的最新进展。在过去的十年中，该领域的活动激增，已经设计出了由金属化合物，光以及布朗斯台德和路易斯酸诱导的吡啶并三唑的新型脱氮反应。结果，已经合成了杂环化合物和官能化的α-甲基吡啶以及生物活性分子。在审查中，重点也放在新反应的机制上。

1引言

2吡啶三唑的环链异构化

3金属催化的反应

3.1 Rh（II）催化

3.2 Rh（III）催化

3.3铜催化

3.4钯催化

3.5其他金属的催化

4无金属反应

5结论

出版历史

收到：2020年6月3日

修订后接受：2020年7月24日

发布日期：
2020年8月25日（在线）

©2020年。Thieme。版权所有

Georg Thieme Verlag
KGRüdigerstraße14，70469斯图加特，德国