Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: efficient synthesis of poly-substituted 1,2,3-triazoles.
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.
Wang
Xiao-Jun
XJ
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, USA. xiao-jun.wang@boehringer-ingelheim.com
Sidhu
Kanwar
K
Zhang
Li
L
Campbell
Scot
S
Haddad
Nizar
N
Reeves
Diana C
DC
Krishnamurthy
Dhileepkumar
D
Senanayake
Chris H
CH
D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D006842:Hydrocarbons, Brominated; D014230:Triazoles