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

D4551

Sigma-Aldrich

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

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

326488

Sigma-Aldrich

Copper, beads, 2-8 mm, ≥99.99% trace metals basis

BCR058

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

266744

Sigma-Aldrich

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

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

72438

Supelco

N,N-Dimethylformamide, analytical standard

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

319937

Sigma-Aldrich

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

494488

Sigma-Aldrich

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

D158550

Sigma-Aldrich

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

GF04898357

Copper, insulated wire, 20m, conductor diameter 0.125mm, insulation thickness 0.01mm, polyimide insulation, 99.99%

GF55575647

Copper, insulated wire, 5m, conductor diameter 0.5mm, insulation thickness 0.025mm, polyimide insulation, 99.99%

GF55859855

Copper, insulated wire, 2m, conductor diameter 1.0mm, insulation thickness 0.25mm, PTFE (polytetrafluoroethylene) insulation

GF13846877

Copper, rod, 100mm, diameter 16mm, as drawn, 99.99+%

GF14145689

Copper, mesh, 600x600mm, nominal aperture 0.38mm, wire diameter 0.25mm, 40x40 wires/inch, open area 37%, plain weave mesh

GF33693194

Copper, insulated wire, 50m, conductor diameter 0.5mm, insulation thickness 0.06mm, polyimide insulation

GF15689818

Copper, insulated wire, 5m, conductor diameter 0.24mm, insulation thickness 0.25mm, PTFE (polytetrafluoroethylene) insulation

GF69546819

Copper, mesh, 100x100mm, nominal aperture 0.38mm, wire diameter 0.25mm, 40x40 wires/inch, open area 37%, plain weave mesh

GF26289939

Copper, mesh, 65x65mm, nominal aperture 0.2mm, thickness 0.004mm, wire diameter 0.0125mm, 118 wires/inch, open area 88%, electro-formed mesh

254177

Sigma-Aldrich

Copper, beads, 2-8 mm, 99.9995% trace metals basis

349208

Sigma-Aldrich

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

326410

Sigma-Aldrich

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349224

Sigma-Aldrich

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

326429

Sigma-Aldrich

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

349151

Sigma-Aldrich

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

349216

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

GF53474980

Copper, tube, 100mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF93436926

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

GF69447280

Copper, tube, 100mm, outside diameter 0.75mm, inside diameter 0.23mm, wall thickness 0.26mm, as drawn, 99.9%