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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, powder, 99.99% trace metals basis

Copper, IRMM^®, certified reference material, 0.1 mm foil

Copper, IRMM^®, certified reference material, 0.5 mm wire

Copper (O), BCR^®, certified reference material, rod

Sigma-Aldrich

Copper, powder (spheroidal), 10-25 μm, 98%

Sigma-Aldrich

Copper, powder, <425 μm, 99.5% trace metals basis

Sigma-Aldrich

Copper, powder (dendritic), <45 μm, 99.7% trace metals basis

Sigma-Aldrich

Copper, foil, thickness 0.25 mm, 99.98% trace metals basis

Sigma-Aldrich

Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

Copper (S, P), BCR^®, certified reference material, chips

USP

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

Copper, wire reel, 2000m, diameter 0.125mm, annealed, 99.9%

Copper, wire reel, 50m, diameter 0.05mm, as drawn, 99.99+%

Copper, wire reel, 25m, diameter 1.0mm, annealed, 99.9%

Copper, wire reel, 50m, diameter 0.04mm, hard, 99.9%

Copper, wire reel, 200m, diameter 1.0mm, annealed, 99.9%

Copper, wire reel, 5m, diameter 0.02mm, hard, 99.99+%

Copper, wire reel, 1m, diameter 0.25mm, as drawn, 99.99+%

Copper, wire reel, 50m, diameter 0.125mm, as drawn, 99.99+%

Copper - O.F.H.C., foil, not light tested, 50x50mm, thickness 0.006mm, hard, 99.95+%

Copper - O.F.H.C., foil, light tested, 300x300mm, thickness 0.05mm, hard, 99.95+%

Copper - O.F.H.C., rod, 200mm, diameter 16mm, as drawn, 99.95+%

Copper - O.F.H.C., rod, 1000mm, diameter 12.7mm, as drawn, 99.95+%

Copper, wire reel, 50m, diameter 0.125mm, annealed, 99.9%

Copper, wire reel, 5m, diameter 0.75mm, as drawn, 99.98+%

Copper - O.F.H.C., foil, 6mm disks, thickness 0.5mm, half hard, 99.95+%

Copper - O.F.H.C., rod, 1000mm, diameter 16mm, as drawn, 99.95+%

Copper - O.F.H.C., rod, 100mm, diameter 25.4mm, as drawn, 99.95+%

Copper - O.F.H.C., foil, 8mm disks, thickness 0.25mm, annealed, 99.95+%