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

BCR058

Continuous cast copper (O), BCR^®, certified reference material, rod

GF74071122

Copper - O.F.H.C., tube, 500mm, outside diameter 4.0mm, inside diameter 3mm, wall thickness 0.5mm, 99.95+%

GF87182657

Copper, tube, 1000mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%

GF41407501

Copper, microfoil, disks, 10mm, thinness 0.25μm, specific density 219.9μg/cm², permanent mylar 3.5μm support, 99.99+%

D158550

Sigma-Aldrich

N,N-Dimethylformamide, ReagentPlus^®, ≥99%

GF07140002

Copper - O.F.H.C., foil, 50x50mm, thickness 2.0mm, half hard, 99.95+%

349151

Sigma-Aldrich

Copper, foil, thickness 0.5 mm, 99.98% trace metals basis

349224

Sigma-Aldrich

Copper, wire, diam. 2.0 mm, 99.999% trace metals basis

266744

Sigma-Aldrich

Copper, foil, thickness 1.0 mm, 99.999% trace metals basis

326429

Sigma-Aldrich

Copper, wire, diam. 0.25 mm, 99.999% trace metals basis

D4551

Sigma-Aldrich

N,N-Dimethylformamide, Molecular Biology, ≥99%

227056

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

349208

Sigma-Aldrich

Copper, foil, thickness 0.025 mm, 99.98% trace metals basis

72438

Supelco

N,N-Dimethylformamide, analytical standard

GF80997889

Copper - O.F.H.C., foil, 1m coil, thickness 0.010mm, coil width 25mm, hard, 99.95+%

GF93055901

Copper - O.F.H.C., foil, 2m coil, thickness 0.025mm, hard, 99.95+%

GF66965956

Copper, wire reel, 1000m, diameter 0.125mm, annealed, 99.9%

GF66681311

Copper - O.F.H.C., foil, light tested, 150x150mm, thickness 0.05mm, hard, 99.95+%

GF42804547

Copper - O.F.H.C., rod, 25mm, diameter 25.4mm, as drawn, 99.99+%

GF75858441

Copper - O.F.H.C., foil, 8mm disks, thickness 0.5mm, half hard, 99.95+%

GF71113823

Copper - O.F.H.C., foil, 50mm disks, thickness 0.5mm, half hard, 99.95+%

GF42873723

Copper - O.F.H.C., foil, 1m coil, thickness 0.010mm, hard, 99.95+%

GF06880507

Copper - O.F.H.C., foil, 6mm disks, thickness 0.1mm, hard, 99.95+%

GF23860032

Copper, wire reel, 5m, diameter 0.05mm, as drawn, 99.99+%

GF14011647

Copper, tube, 500mm, outside diameter 3.0mm, inside diameter 1.2mm, wall thickness 0.9mm, as drawn, 99.9%

GF16888854

Copper, wire reel, 50m, diameter 0.1mm, annealed, 99.9%

GF02949486

Copper - O.F.H.C., foil, 2m coil, thickness 0.05mm, hard, 99.95+%

GF50461927

Copper - O.F.H.C., tube, 500mm, outside diameter 0.635mm, inside diameter 0.275mm, wall thickness 0.18mm, 99.95+%

GF46297468

Copper, tube, 500mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%

GF03713059

Copper - O.F.H.C., sheet, 300x300mm, thickness 3.0mm, 99.95+%