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

72438

Supelco

N,N-Dimethylformamide, analytical standard

326488

Sigma-Aldrich

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

266744

Sigma-Aldrich

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

254177

Sigma-Aldrich

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

BCR058

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

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

349208

Sigma-Aldrich

Copper, foil, thickness 0.025 mm, 99.98% 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%

326410

Sigma-Aldrich

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

227056

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

D4551

Sigma-Aldrich

N,N-Dimethylformamide, for molecular biology, ≥99%

GF13846877

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

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

349224

Sigma-Aldrich

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

GF89142701

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

GF87182657

Copper, tube, 1000mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%

GF16694006

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

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%

D158550

Sigma-Aldrich

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

319937

Sigma-Aldrich

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

GF94804779

Copper - O.F.H.C., foil, 50mm disks, thickness 0.25mm, half hard, 99.95+%

GF47171033

Copper, wire reel, 100m, diameter 0.025mm, as drawn, 99.99+%

GF10253179

Copper - O.F.H.C., foil, 25mm disks, thickness 0.7mm, half hard, 99.95+%

GF14058705

Copper, wire reel, 0.5m, diameter 0.5mm, as drawn, 99.999%

GF71113823

Copper - O.F.H.C., foil, 50mm disks, thickness 0.5mm, half hard, 99.95+%

GF53533201

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