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

D158550

Sigma-Aldrich

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

494488

Sigma-Aldrich

N,N-Dimethylformamide, biotech. grade, ≥99.9%

319937

Sigma-Aldrich

N,N-Dimethylformamide, ACS reagent, ≥99.8%

33120

Sigma-Aldrich

N,N-Dimethylformamide, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.8% (GC)

270547

Sigma-Aldrich

N,N-Dimethylformamide, suitable for HPLC, ≥99.9%

GF28659471

Copper, wire reel, 0.2m, diameter 1.0mm, as drawn, 99.99+%

GF41811724

Copper - O.F.H.C., foil, 10mm disks, thickness 0.25mm, annealed, 99.95+%

GF10425169

Copper - O.F.H.C., foil, 20m coil, thickness 0.010mm, coil width 25mm, hard, 99.95+%

GF68687038

Copper - O.F.H.C., foil, 10m coil, thickness 0.1mm, hard, 99.95+%

GF87158650

Copper, tube, 500mm, outside diameter 1.0mm, inside diameter 0.24mm, wall thickness 0.38mm, as drawn, 99.9%

GF53132330

Copper - O.F.H.C., foil, 50mm disks, thickness 0.075mm, half hard, 99.95+%

GF93055901

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

GF09290426

Copper - O.F.H.C., foil, 300x300mm, thickness, 0.5mm, half hard, flattened, 99.95+%

GF17037031

Copper - O.F.H.C., foil, 10mm disks, thickness 0.075mm, half hard, 99.95+%

GF58516285

Copper - O.F.H.C., foil, 20m coil, thickness 0.05mm, coil width 10mm, annealed, 99.95+%

GF93757786

Copper - O.F.H.C., foil, 15mm disks, thickness 0.125mm, hard, 99.95+%

GF42873723

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

GF32269259

Copper - O.F.H.C., foil, 4mm disks, thickness 0.010mm, hard, 99.95+%

GF38369100

Copper - O.F.H.C., foil, 15mm disks, thickness 1.0mm, half hard, 99.95+%

GF46297468

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

GF07953644

Copper - O.F.H.C., foil, 10mm disks, thickness 0.1mm, hard, 99.95+%

GF01396425

Copper - O.F.H.C., foil, 10m coil, thickness 0.05mm, hard, 99.95+%

GF19506955

Copper - O.F.H.C., foil, 10mm disks, thickness 1.0mm, half hard, 99.95+%

GF24248864

Copper - O.F.H.C., foil, 2m coil, thickness 0.20mm, hard, 99.95+%

GF08771766

Copper - O.F.H.C., foil, 1m coil, thickness 0.1mm, half hard, 99.95+%

GF03331268

Copper, tube, 500mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%

GF52221271

Copper - O.F.H.C., foil, 15mm disks, thickness 0.25mm, annealed, 99.95+%

GF23409491

Copper - O.F.H.C., foil, 10mm disks, thickness 0.05mm, hard, 99.95+%

GF25261657

Copper - O.F.H.C., foil, 1m coil, thickness 0.05mm, coil width 10mm, annealed, 99.95+%

GF98944600

Copper - O.F.H.C., foil, 25mm disks, thickness 0.025mm, hard, 99.95+%