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, for molecular biology, ≥99%

266744

Sigma-Aldrich

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

BCR058

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

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

72438

Supelco

N,N-Dimethylformamide, analytical standard

326488

Sigma-Aldrich

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

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

227056

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

GF71474249

Copper - O.F.H.C., foil, 300x300mm, thickness 0.1mm, half hard, 99.95+%

GF37945569

Copper, insulated wire, 1m, conductor diameter 0.45mm, insulation thickness 0.25mm, PTFE (polytetrafluoroethylene) insulation

GF35043702

Copper, insulated wire, 10m, conductor diameter 0.5mm, insulation thickness 0.025mm, polyimide insulation, 99.99%

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

GF15993423

Copper - O.F.H.C., foil, 0.5m coil, thickness 0.1mm, coil width 100mm, hard, 99.95+%

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Copper, insulated wire, 250m, conductor diameter 0.05mm, insulation thickness 0.002mm, 2 micron polyesterimide insulation, 99.9%

GF08487456

Copper - O.F.H.C., foil, 300x300mm, thickness 0.1mm, hard, 99.95+%

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Copper, insulated wire, 1m, conductor diameter 1.0mm, insulation thickness 0.25mm, PTFE (polytetrafluoroethylene) insulation

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Copper, insulated wire, 20m, conductor diameter 0.025mm, insulation thickness 0.005mm, polyurethane insulation, 99.99%

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Copper - O.F.H.C., foil, 25x25mm, thickness 0.25mm, annealed, 99.95+%

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Copper, insulated wire, 100m, conductor diameter 0.5mm, insulation thickness 0.06mm, polyimide insulation

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Copper, insulated wire, 50m, conductor diameter 1.0mm, insulation thickness 0.25mm, PTFE (polytetrafluoroethylene) insulation

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Copper, insulated wire, 10m, conductor diameter 1.0mm, insulation thickness 0.25mm, PTFE (polytetrafluoroethylene) insulation

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Copper, rod, 100mm, diameter 6.35mm, as drawn, 99.999%