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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
Sigma-Aldrich
Copper, powder, <425 μm, 99.5% trace metals basis
Sigma-Aldrich
Copper, foil, thickness 0.25 mm, 99.98% trace metals basis
Sigma-Aldrich
Copper, shot, −3-+14 mesh, 99%
Sigma-Aldrich
Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%
Sigma-Aldrich
Copper, powder (spheroidal), 10-25 μm, 98%
Copper (O), BCR®, certified reference material, rod
Copper, IRMM®, certified reference material, 0.1 mm foil
Copper (S, P), BCR®, certified reference material, chips
Copper, IRMM®, certified reference material, 0.5 mm wire
USP
Residual Solvent Class 2 - N,N-Dimethylformamide, United States Pharmacopeia (USP) Reference Standard
Copper, tube, 1000mm, outside diameter 4.0mm, inside diameter 3.2mm, wall thickness 0.4mm, as drawn, 99.9%
Copper, rod, 100mm, diameter 12.7mm, as drawn, 99.99+%
Copper, insulated wire, 20m, conductor diameter 0.5mm, insulation thickness 0.025mm, polyimide insulation, 99.99%
Copper, wire reel, 2m, diameter 0.25mm, as drawn, 99.99+%
Copper, insulated wire, 2m, conductor diameter 0.1mm, insulation thickness 0.01mm, PTFE (polytetrafluoroethylene) insulation, 99.99%
Copper, wire reel, 0.1m, diameter 0.1mm, aluminum cladding, outside diameter 0.25mm, 99.9%
Copper, wire reel, 25m, diameter 0.125mm, as drawn, 99.99+%
Copper, rod, 1000mm, diameter 4.8mm, as drawn, 99.99+%
Copper, wire reel, 50m, diameter 0.5mm, annealed, silver plated, 99.9%
Copper, microfoil, disks, 25mm, thinness 0.5μm, specific density 448μg/cm2, permanent mylar 3.5μm support, 99.99+%
Copper, rod, 100mm, diameter 2.0mm, as drawn, 99.99+%
Copper, wire reel, 25m, diameter 0.5mm, as drawn, 99.98+%
Copper, insulated wire, 10m, conductor diameter 0.125mm, insulation thickness 0.002mm, 2 micron polyesterimide insulation, 99.9%
Copper, wire reel, 50m, diameter 0.04mm, hard, 99.9%
Copper, wire reel, 25m, diameter 1.0mm, annealed, 99.9%
Copper, tube, 100mm, outside diameter 4.0mm, inside diameter 3.2mm, wall thickness 0.4mm, as drawn, 99.9%
Copper, tube, 100mm, outside diameter 5.0mm, inside diameter 4mm, wall thickness 0.5mm, as drawn, 99.9%
Copper, microfoil, disks, 10mm, thinness 0.1μm, specific density 86.2μg/cm2, permanent mylar 3.5μm support, 99.99+%
Copper, wire reel, 5m, diameter 0.02mm, annealed, 99.99%