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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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Supelco

N,N-Dimethylformamide, analytical standard

Sigma-Aldrich

Copper, powder, <75 μm, 99%

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

Sigma-Aldrich

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

Copper, rod, 50mm, diameter 12.7mm, as drawn, 99.99+%

Copper, rod, 200mm, diameter 4.8mm, hard, 99.9%

Copper, tube, 1000mm, outside diameter 5.0mm, inside diameter 4mm, wall thickness 0.5mm, as drawn, 99.9%

Sigma-Aldrich

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

Copper - O.F.H.C., foil, 50mm disks, thickness 0.010mm, hard, 99.95+%

Copper - O.F.H.C., foil, 6mm disks, thickness 0.006mm, hard, 99.95+%

Copper, tube, 500mm, outside diameter 5.0mm, inside diameter 4mm, wall thickness 0.5mm, as drawn, 99.9%

Copper, wire reel, 2000m, diameter 0.075mm, annealed, 99.9%

Copper, wire reel, 1000m, diameter 0.04mm, hard, 99.9%

Copper, wire reel, 50m, diameter 0.25mm, as drawn, 99.99+%

Copper - O.F.H.C., foil, 6mm disks, thickness 0.075mm, half hard, 99.95+%

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

Copper, wire reel, 100m, diameter 0.075mm, annealed, 99.9%

Copper, wire reel, 1000m, diameter 0.05mm, annealed, 99.9%

Copper, wire reel, 2m, diameter 0.75mm, as drawn, 99.98+%