» Articles » PMID: 38213840

Synthesis of -acyl Carbazoles, Phenoxazines and Acridines from Cyclic Diaryliodonium Salts

Overview
Specialty Chemistry
Date 2024 Jan 12
PMID 38213840
Authors
Affiliations
Soon will be listed here.
Abstract

-Acyl carbazoles can be efficiently produced through a single-step process using amides and cyclic diaryliodonium triflates. This convenient reaction is facilitated by copper iodide in -xylene, using the commonly found activating ligand diglyme. We have tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates. Beyond carbazoles, we also produced a variety of other -heterocycles, such as acridines, phenoxazines, or phenazines, showcasing the robustness of our technique. In a broader sense, this new method creates two C-N bonds simultaneously based on a mono-halogenated starting material, thus allowing heterocycle formation with diminished halogen waste

References
1.
Chen C, Chi Z, Chong K, Batsanov A, Yang Z, Mao Z . Carbazole isomers induce ultralong organic phosphorescence. Nat Mater. 2020; 20(2):175-180. DOI: 10.1038/s41563-020-0797-2. View

2.
Bielawski M, Olofsson B . High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides. Chem Commun (Camb). 2007; (24):2521-3. DOI: 10.1039/b701864a. View

3.
Wang M, Fan Q, Jiang X . Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole. Org Lett. 2017; 20(1):216-219. DOI: 10.1021/acs.orglett.7b03564. View

4.
Merritt E, Olofsson B . Diaryliodonium salts: a journey from obscurity to fame. Angew Chem Int Ed Engl. 2009; 48(48):9052-70. DOI: 10.1002/anie.200904689. View

5.
Utaipan T, Athipornchai A, Suksamrarn A, Jirachotikoon C, Yuan X, Lertcanawanichakul M . Carbazole alkaloids from Murraya koenigii trigger apoptosis and autophagic flux inhibition in human oral squamous cell carcinoma cells. J Nat Med. 2016; 71(1):158-169. DOI: 10.1007/s11418-016-1045-6. View