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Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: efficient synthesis of poly-substituted 1,2,3-triazoles. 2009

Xiao-Jun Wang, and Kanwar Sidhu, and Li Zhang, and Scot Campbell, and Nizar Haddad, and Diana C Reeves, and Dhileepkumar Krishnamurthy, and Chris H Senanayake
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, USA. xiao-jun.wang@boehringer-ingelheim.com

Reaction of 4-bromo-NH-1,2,3-triazoles 2 with alkyl halides in the presence of K(2)CO(3) in DMF produced the corresponding 2-substituted 4-bromo-1,2,3-triazoles 5 in a regioselective process. Subsequent Suzuki cross-coupling reaction of these bromides provided an efficient synthesis of 2,4,5-trisubstituted triazoles 3. In addition, reduction of the bromotriazoles by hydrogenation furnished an efficient synthesis of 2,4-disubstituted triazoles 8.

UI MeSH Term Description Entries
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D006842 Hydrocarbons, Brominated Hydrocarbon compounds with one or more HYDROGEN atoms substituted with BROMINE. Brominated Hydrocarbons
D000478 Alkylation The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group. Alkylations
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D020650 Combinatorial Chemistry Techniques A technology, in which sets of reactions for solution or solid-phase synthesis, is used to create molecular libraries for analysis of compounds on a large scale. Chemistry Techniques, Combinatorial,Techniques, Combinatorial Chemistry,Chemistry Technic, Combinatorial,Chemistry Technics, Combinatorial,Chemistry Technique, Combinatorial,Combinatorial Chemistry Technic,Combinatorial Chemistry Technics,Combinatorial Chemistry Technique,Technic, Combinatorial Chemistry,Technics, Combinatorial Chemistry,Technique, Combinatorial Chemistry

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