BIOMAT Database Logo BIOMAT Database Logo

Metal-Free Synthesis of 1,5-Disubstituted 1,2,3-Triazoles. 2021

Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky prospekt, Peterhof 198504, Russia.

A three-component synthesis of 1,5-disubstituted 1,2,3-triazoles from α-acetyl-α-diazomethane sulfonamides, primary aliphatic amines, and aromatic aldehydes is presented. The 1,2,3-triazoles can be accessed in two alternative variants, depending on the substitutions in the sulfonamide portion of the diazo reagent. In one variant, intermediate 1,2,3-triazoline-4-sulfonamides are isolated chromatographically and then subjected to thermally promoted aromatization with elimination of sulfur(IV) oxide and amine. In the other variant, both chemical transformations take place in a single step conducted at room temperature.

UI MeSH Term Description Entries
D008670 Metals Electropositive chemical elements characterized by ductility, malleability, luster, and conductance of heat and electricity. They can replace the hydrogen of an acid and form bases with hydroxyl radicals. (Grant & Hackh's Chemical Dictionary, 5th ed) Metal
D000447 Aldehydes Organic compounds containing a carbonyl group in the form -CHO. Aldehyde
D000588 Amines A group of compounds derived from ammonia by substituting organic radicals for the hydrogens. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amine
D013449 Sulfonamides A group of compounds that contain the structure SO2NH2. Sulfonamide,Sulfonamide Mixture,Sulfonamide Mixtures,Mixture, Sulfonamide,Mixtures, Sulfonamide
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole

Related Publications

Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
An Organocatalytic Regiospecific Synthesis of 1,5-Disubstituted 4-Thio-1,2,3-triazoles and 1,5-Disubstituted 1,2,3-Triazoles.
November 2015, Chemistry (Weinheim an der Bergstrasse, Germany),
Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
A metal-free multicomponent cascade reaction for the regiospecific synthesis of 1,5-disubstituted 1,2,3-triazoles.
December 2013, Angewandte Chemie (International ed. in English),
Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
Transition-metal-free catalytic synthesis of 1,5-diaryl-1,2,3-triazoles.
October 2010, Organic letters,
Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
Ionic liquid-phase synthesis of 1,5-disubstituted 1,2,3-triazoles.
August 2014, ACS combinatorial science,
Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited.
April 2004, Organic letters,
Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
Copper-catalyzed decarboxylative regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles.
March 2018, Chemical communications (Cambridge, England),
Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
A Metal- and Azide-Free Multicomponent Assembly toward Regioselective Construction of 1,5-Disubstituted 1,2,3-Triazoles.
September 2015, The Journal of organic chemistry,
Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
Are 1,4- and 1,5-disubstituted 1,2,3-triazoles good pharmacophoric groups?
November 2014, ChemMedChem,
Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
Regioselective synthesis of 4-fluoro-1,5-disubstituted-1,2,3-triazoles from synthetic surrogates of α-fluoroalkynes.
February 2020, Chemical communications (Cambridge, England),
Andrey Bubyrev, and Ksenia Malkova, and Grigory Kantin, and Dmitry Dar'in, and Mikhail Krasavin
Aerobic Oxidative Cycloaddition of α-Chlorotosylhydrazones with Arylamines: General Chemoselective Construction of 1,4-Disubstituted and 1,5-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions.
June 2015, Organic letters,
Copied contents to your clipboard!