TY - JOUR

T1 - Recent Advances in Denitrogenative Reactions of Pyridotriazoles

AU - Filippov, Ilya P.

AU - Titov, Gleb D.

AU - Rostovskii, Nikolai V.

N1 - Publisher Copyright: © 2020 BMJ Publishing Group. All rights reserved.

PY - 2020/12/1

Y1 - 2020/12/1

N2 - 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 Bronsted 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.

AB - 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 Bronsted 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.

KW - 1,2,3-triazoles

KW - carbenes

KW - catalysis

KW - diazo compounds

KW - nitrogen heterocycles

KW - pyridotriazoles

KW - α-picolines

KW - ONE-POT SYNTHESIS

KW - RH-CATALYZED TRANSANNULATION

KW - TRIAZOLOPYRIDINES

KW - ALKYNES

KW - alpha-picolines

KW - 1,2,3-TRIAZOLES

KW - METAL

KW - TRANSFORMATIONS

UR - http://www.scopus.com/inward/record.url?scp=85090941261&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/8f62b9a4-ca17-38cd-9195-e30d5da1040a/

U2 - 10.1055/s-0040-1707254

DO - 10.1055/s-0040-1707254

M3 - Review article

AN - SCOPUS:85090941261

VL - 52

SP - 3564

EP - 3576

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 23

ER -