TY - JOUR
T1 - Efficient multicomponent synthesis of mono-, bis-, and tris-1,2,3-triazoles supported by hydroxybenzene scaffolds
AU - Mendoza-Espinosa, Daniel
AU - Negrón-Silva, Guillermo E.
AU - Lomas-Romero, Leticia
AU - Gutiérrez-Carrillo, Atilano
AU - Soto-Castro, Delia
PY - 2013
Y1 - 2013
N2 - A versatile one-pot synthesis of a series of mono-, bis- and tris-1,2,3-triazoles supported by commercially available hydroxybenzene scaffolds has been developed employing click chemistry. The multicomponent copper(I)-catalyzed 1,3-dipolar cycloaddition of sodium azide, propargyl bromide, and a para-substituted benzyl derivative yields N-benzyl-functionalized triazoles featuring several electron-donating or electron-withdrawing groups. Despite the preparation of highly substituted molecules, reaction conditions that provides good yields involved room temperature, times that oscillate between 16 and 24 hours, and catalyst loads ranging from 5-10 mol%. The present methodology could be useful for the building up of multi-triazole libraries easily tunable with donor or attractor functional groups.
AB - A versatile one-pot synthesis of a series of mono-, bis- and tris-1,2,3-triazoles supported by commercially available hydroxybenzene scaffolds has been developed employing click chemistry. The multicomponent copper(I)-catalyzed 1,3-dipolar cycloaddition of sodium azide, propargyl bromide, and a para-substituted benzyl derivative yields N-benzyl-functionalized triazoles featuring several electron-donating or electron-withdrawing groups. Despite the preparation of highly substituted molecules, reaction conditions that provides good yields involved room temperature, times that oscillate between 16 and 24 hours, and catalyst loads ranging from 5-10 mol%. The present methodology could be useful for the building up of multi-triazole libraries easily tunable with donor or attractor functional groups.
KW - catalysis
KW - click chemistry
KW - hydroxybenzene
KW - multi-triazoles
KW - one-pot synthesis
UR - http://www.scopus.com/inward/record.url?scp=84883134479&partnerID=8YFLogxK
U2 - 10.1055/s-0033-1339376
DO - 10.1055/s-0033-1339376
M3 - Artículo
SN - 0039-7881
VL - 45
SP - 2431
EP - 2437
JO - Synthesis (Germany)
JF - Synthesis (Germany)
IS - 17
M1 - SS-2013-M0333-OP
ER -