Choline Azide: New Reagent and Ionic Liquid in Catalyst‐Free and Solvent‐Free Synthesis of 5‐Substituted‐1H‐Tetrazoles: A Triple Function Reagent

Abstract

This article is dedicated to the memory of Mohsen Hojaji.An efficient and green route for the synthesis of 5-substituted-1H-tetrazoles using choline azide as a new azidation reagent in solvent-free and catalyst-free conditions, is reported for the first time. The noteworthy aspects of this high-yield and costeffective reaction are simple methodology, mild reaction conditions, easy work-up procedure, low reaction time, and specially using choline azide as an effective alternative to hazardous azidation agent.[a] Dr.

Recent Advances in the Synthesis of 5-Substituted 1H-Tetrazoles: A Complete Survey (2013–2018)

“…A catalyst-free and solvent-free synthesis of 5-substituted 1H-tetrazoles in good to excellent yields (75-95%) from nitriles using a new azidation reagent and the ionic liquid choline azide for 3-6 hours was reported by Heydari and co-workers (Scheme 56). 100 Choline azide is an effective, green, and safe azide source that can be recycled and reused for further tetrazole syntheses. The maximum yield was achieved when 4-nitrobenzonitrile was used.…”

A Facile Approach to Catalyst-Free Cyanation and Azidation of ­Organic Compounds and a One-Pot Preparation of 5-Substituted 1H-Tetrazoles by Using a Dimethyl Sulfoxide–Nitric Acid Combination

“…Thus, efforts continue to be made to find alternative methods. Among recent developments have been the use of Pd-SMTU@boehmite (SMTU = S-methylisothiourea), 26 Ni(OH) 2 nanoparticles, 27 choline azide, 28 MCM-41@AMPD@Zn (AMPD = 2-amino-2-methylpropane-1,3-diol), 29 and Sm@l-MSN (l-MSN = large-pore mesoporous silica nanoparticles), 30 or Cu-MOF nanocatalysts. 31 De Luca et al used a DMF-2,4,6-trichloro-1,3,5-triazine complex for the efficient transformation of oximes into nitriles under mild conditions.…”

Folic‐Acid‐Functionalized Magnetic Nanoparticles as Green and Magnetic Recyclable Catalyst for the Synthesis of 4‐Aryl‐NH‐1,2,3‐triazoles in a Green Media

“…Synthesis of choline azide has poorly developed. This is made up of choline chloride, which is green media and used as a deep eutectic solvent . In continuation of our laboratory work on environmental procedures now we expose the catalytic activity of Fe 3 O 4 @Folic acid nanoparticle as a green and heterogeneous catalyst for the one‐pot synthesis of 4‐aryl‐NH‐1,2,3‐triazoles via cycloaddition of an aromatic aldehyde, nitromethane in choline azide.…”