title: Direct, Regioselective N-Alkylation of 1,3-Azoles.
abstract: Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.
authors.affiliation: Medicinal Chemsitry Department, Amgen, Inc. , 360 Binney Street, Cambridge, Massachusetts 02142, United States.
authors.forename: Shuai
authors.initials: S
authors.lastname: Chen
authors.affiliation: Medicinal Chemsitry Department, Amgen, Inc. , 360 Binney Street, Cambridge, Massachusetts 02142, United States.
authors.forename: Russell F
authors.initials: RF
authors.lastname: Graceffa
authors.affiliation: Medicinal Chemsitry Department, Amgen, Inc. , 360 Binney Street, Cambridge, Massachusetts 02142, United States.
authors.forename: Alessandro A
authors.initials: AA
authors.lastname: Boezio
mesh_terms: D000478:Alkylation; D001393:Azoles / Q000737:chemistry*; D002384:Catalysis; D008274:Magnesium / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001393:Azoles; D009942:Organometallic Compounds; D008274:Magnesium