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  • A novel straightforward synthesis of 2,4-disubstituted-1,3,5-triazines via aerobic copper-catalyzed cyclization of amidines with DMF.

A novel straightforward synthesis of 2,4-disubstituted-1,3,5-triazines via aerobic copper-catalyzed cyclization of amidines with DMF.

Organic letters (2014-06-17)
Xiaowen Xu, Min Zhang, Huanfeng Jiang, Jia Zheng, Yiqun Li
ABSTRACT

A novel straightforward synthesis of both symmetrical and unsymmetrical 2,4-disubstituted-1,3,5-triazines via aerobic copper-catalyzed cyclization of amidines with DMF as a one-carbon synthon has been developed. The presented method allows synthesizing the products that are currently inaccessible or challenging to prepare with the advantages of operational simplicity, broad substrate scope, and no need for prefunctionalized reagents, making it a highly practical approach to access various 2,4-disubstituted-1,3,5-triazines.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
N,N-Dimethylformamide, biotech. grade, ≥99.9%
Sigma-Aldrich
N,N-Dimethylformamide, ACS reagent, ≥99.8%
Sigma-Aldrich
N,N-Dimethylformamide, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.8% (GC)
Sigma-Aldrich
N,N-Dimethylformamide, ReagentPlus®, ≥99%
Copper - O.F.H.C., foil, 4mm disks, thickness 0.006mm, hard, 99.95+%
Copper - O.F.H.C., foil, 2m coil, thickness 0.05mm, annealed, 99.95+%
Copper - O.F.H.C., foil, 10m coil, thickness 0.05mm, hard, 99.95+%
Copper - O.F.H.C., foil, 4mm disks, thickness 0.010mm, hard, 99.95+%
Copper - O.F.H.C., foil, 10m coil, thickness 0.075mm, half hard, 99.95+%
Copper - O.F.H.C., foil, 6mm disks, thickness 0.075mm, half hard, 99.95+%
Copper - O.F.H.C., foil, 5m coil, thickness 0.05mm, coil width 300mm, half hard, 99.95+%
Copper - O.F.H.C., foil, 15mm disks, thickness 0.125mm, hard, 99.95+%
Copper, tube, 500mm, outside diameter 4.0mm, inside diameter 3.2mm, wall thickness 0.4mm, as drawn, 99.9%
Copper - O.F.H.C., foil, 5m coil, thickness 0.1mm, hard, 99.95+%
Copper - O.F.H.C., foil, 1m coil, thickness 0.010mm, hard, 99.95+%
Copper - O.F.H.C., foil, 2m coil, thickness 0.125mm, hard, 99.95+%
Copper - O.F.H.C., foil, 10m coil, thickness 0.1mm, coil width 100mm, hard, 99.95+%
Copper - O.F.H.C., foil, 25mm disks, thickness 0.075mm, half hard, 99.95+%
Copper - O.F.H.C., foil, 50mm disks, thickness 0.010mm, hard, 99.95+%
Copper, tube, 500mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%
Copper, tube, 500mm, outside diameter 5.0mm, inside diameter 4mm, wall thickness 0.5mm, as drawn, 99.9%
Copper - O.F.H.C., foil, 25mm disks, thickness 0.125mm, hard, 99.95+%
Copper - O.F.H.C., foil, 10mm disks, thickness 0.025mm, hard, 99.95+%
Copper - O.F.H.C., foil, 5m coil, thickness 0.1mm, coil width 100mm, hard, 99.95+%
Copper - O.F.H.C., foil, 4mm disks, thickness 0.025mm, hard, 99.95+%
Copper - O.F.H.C., foil, 10mm disks, thickness 0.1mm, hard, 99.95+%
Copper, tube, 500mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%
Copper - O.F.H.C., foil, 5m coil, thickness 0.075mm, half hard, 99.95+%
Copper - O.F.H.C., foil, 50mm disks, thickness 0.05mm, hard, 99.95+%
Copper - O.F.H.C., foil, 1m coil, thickness 0.1mm, half hard, 99.95+%