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

227056

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

266744

Sigma-Aldrich

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

349208

Sigma-Aldrich

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

326410

Sigma-Aldrich

Copper, wire, diam. 0.64 mm, 99.995% trace metals basis

GF40548180

Copper, sphere, 200pcs, diameter 3.0mm, precision sphere grade 200

GF16694006

Copper, rod, 50mm, diameter 6.35mm, as drawn, 99.999%

GF37804901

Copper, tube, 1000mm, outside diameter 1.2mm, inside diameter 0.56mm, wall thickness 0.32mm, as drawn, 99.9%

GF46821382

Copper, tube, 100mm, outside diameter 1.75mm, inside diameter 0.33mm, wall thickness 0.71mm, as drawn, 99.9%

GF20661083

Copper, tube, 1000mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF60058346

Copper, sphere, 1000pcs, diameter 3.0mm, precision sphere grade 200

GF93436926

Copper, tube, 1000mm, outside diameter 0.95mm, inside diameter 0.29mm, wall thickness 0.33mm, as drawn, 99.9%

GF00529040

Copper, sphere, 100pcs, diameter 3.0mm, precision sphere grade 200

GF53960283

Copper - O.F.H.C., foil, 150x150mm, thickness 0.25mm, annealed, 99.95+%

GF56545386

Copper - O.F.H.C., foil, 100x100mm, thickness 0.7mm, half hard, 99.95+%

GF31656832

Copper - O.F.H.C., wire reel, 20m, diameter 0.80mm, as drawn, 99.95+%

GF46869777

Copper - O.F.H.C., foil, 100x100mm, thickness 0.125mm, hard, 99.95+%

GF40203841

Copper - O.F.H.C., foil, 0.5m coil, thickness 0.125mm, hard, 99.95+%

GF83531527

Copper - O.F.H.C., wire reel, 50m, diameter 0.5mm, as drawn, 99.95+%

GF95874722

Copper - O.F.H.C., foil, 100x100mm, thickness 1.0mm, half hard, 99.95+%

GF47876541

Copper - O.F.H.C., tube, 500mm, outside diameter 10mm, inside diameter 8mm, wall thickness 1.0mm, 99.95+%

GF06542153

Copper - O.F.H.C., wire reel, 100m, diameter 0.25mm, as drawn, 99.95+%

GF70390526

Copper - O.F.H.C., wire reel, 10m, diameter 1.0mm, as drawn, 99.95+%

GF92500477

Copper - O.F.H.C., foil, 100x100mm, thickness 2.0mm, half hard, 99.95+%

GF58721632

Copper - O.F.H.C., foil, 150x150mm, thickness 0.125mm, hard, 99.95+%

GF39562601

Copper - O.F.H.C., tube, 500mm, outside diameter 3.2mm, inside diameter 2.4mm, wall thickness 0.4mm, 99.95+%

GF56507373

Copper - O.F.H.C., wire reel, 20m, diameter 2.0mm, hard, 99.95+%

GF72618903

Copper - O.F.H.C., wire reel, 100m, diameter 0.75mm, as drawn, 99.95+%

GF96361263

Copper - O.F.H.C., foil, 100x100mm, thickness 0.1mm, half hard, 99.95+%