Recent Developments in the Synthesis of Nitrogen-Containing Heterocycles through C–H/N–H Bond Functionalizations and Oxidative Cyclization

Abstract

The synthesis and structure of nitrogen-containing heterocycles are fascinating because these compounds have a great richness of structural, physicochemical, and biological properties. Therefore, the development of improved ways for the synthesis of polyfunctional nitrogen-containing heterocycles continues to be a challenging goal. This account describes developments in the discovery of C–H/N–H bond functionalization and oxidative cyclization procedures for the synthesis of nitrogen-containing heterocycles (aziridines, indoles, indolizines, triazoles, imidazoles, oxazoles, thiazoles, quinoxalines, triazines, and pyridines) in our laboratories during the last 15 years.1 Introduction2 Synthesis of Aziridines3 Synthesis of Indoles and Indolizines4 Synthesis of Triazoles5 Synthesis of Imidazoles6 Synthesis of Oxazoles and Thiazoles7 Synthesis of Quinoxalines, Triazines, and Pyridines8 Conclusion and Outlook

Fluorescent indolizine derivative YI-13 detects amyloid-β monomers, dimers, and plaques in the brain of 5XFAD Alzheimer transgenic mouse model

“…Among them, 23 YI compounds were previously reported chemicals and YI-09 , YI-10 , and YI-23 were newly designed [ 11 ]. Indolizine, an isomer of indole, consists of 5- and 6-membered heterocyclic rings with a nitrogen atom [ 12 ]. Since compounds containing indolizine moiety possess a broad spectrum of valuable pharmacological activities such as anti-inflammatory, antimicrobial, anticancer, and antioxidant properties, various strategies for generating novel collections with indolizine scaffold have been developed [ 13 , 14 ].…”

A comparison of the catalytic efficiency of copper-based bimetallic nanoparticles in the click reactions

“…Triazoles, as a type of significantly useful N -heterocycles, 1–5 have been widely applied in fluorescent materials, drug discovery, chemosensing, biochemistry, dendrimers, agricultural products, materials science, corrosion-retarding agents, dyes, and polymer chemistry, 6–8 due to the physically and chemically inertness against reduction, oxidation and hydrolysis under basic or acidic conditions. 9 Plenty of methods have been developed for the synthesis of 1,2,3-triazoles.…”

Recent Advances in Enantioselective Photochemical Reactions of Stabilized Diazo Compounds

“…Since its chemistry has existed for more than a century [2], diazo compounds have been rendered to be versatile building blocks and will continue to play an important role in organic synthesis. Generally, their thermal, photoinitiated, or metal-catalyzed decomposition leads to the corresponding carbenes and metal carbenoids, which can subsequently undergo various transformations, including insertion reactions to C-H, O-H, Si-H, N-H, S-H bonds, cyclopropanation, Wolff rearrangement, addition to forming a ylide with a heteroatom and radical reactions [3,4,5,6,7,8,9,10,11,12,13]. Among various diazo compounds, stabilized diazo compounds are common reaction starting materials owing to their easier preparation and handling, as well as the high reactivity for elaborating into different new molecules [8,14].…”