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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

Supelco

N,N-Dimethylformamide, analytical standard

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Copper, powder, <75 μm, 99%

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

Sigma-Aldrich

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

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

USP

Residual Solvent Class 2 - N,N-Dimethylformamide, United States Pharmacopeia (USP) Reference Standard

Sigma-Aldrich

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

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

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

Copper, tube, 1000mm, outside diameter 0.75mm, inside diameter 0.23mm, wall thickness 0.26mm, as drawn, 99.9%

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

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

Copper - O.F.H.C., foil, 150x150mm, thickness 0.25mm, annealed, 99.95+%

Copper - O.F.H.C., wire reel, 20m, diameter 2.5mm, hard, 99.95+%

Copper - O.F.H.C., tube, 100mm, outside diameter 2.54mm, inside diameter 1.54mm, wall thickness 0.5mm, 99.95+%

Copper - O.F.H.C., wire reel, 100m, diameter 0.80mm, as drawn, 99.95+%

Copper - O.F.H.C., foil, 100x100mm, thickness 0.7mm, half hard, 99.95+%

Copper - O.F.H.C., foil, 100x100mm, thickness 0.125mm, hard, 99.95+%

Copper - O.F.H.C., foil, 100x100mm, thickness 0.20mm, hard, 99.95+%