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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
N,N-Dimethylformamide, biotech. grade, ≥99.9%
Sigma-Aldrich
N,N-Dimethylformamide, ACS reagent, ≥99.8%
Sigma-Aldrich
N,N-Dimethylformamide, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.8% (GC)
Sigma-Aldrich
N,N-Dimethylformamide, ReagentPlus®, ≥99%
Copper - O.F.H.C., foil, 4mm disks, thickness 0.006mm, hard, 99.95+%
Copper, wire reel, 1000m, diameter 0.125mm, annealed, 99.9%
Copper, wire reel, 500m, diameter 0.25mm, annealed, 99.9%
Copper, wire reel, 500m, diameter 0.5mm, annealed, 99.9%
Copper, wire reel, 10m, diameter 0.5mm, annealed, 99.9%
Copper, wire reel, 100m, diameter 0.075mm, annealed, 99.9%
Copper, wire reel, 20m, diameter 1.0mm, as drawn, 99.98+%
Copper, wire reel, 100m, diameter 0.15mm, annealed, silver plated, 99.9%
Copper, tube, 500mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%
Copper, wire reel, 1000m, diameter 0.05mm, annealed, 99.9%
Copper, tube, 500mm, outside diameter 3.0mm, inside diameter 1.2mm, wall thickness 0.9mm, as drawn, 99.9%
Copper - O.F.H.C., foil, 20m coil, thickness 0.010mm, coil width 25mm, hard, 99.95+%
Copper, wire reel, 250m, diameter 0.04mm, annealed, 99.9%
Copper - O.F.H.C., foil, 300x300mm, thickness, 0.5mm, half hard, flattened, 99.95+%
Copper, wire reel, 1000m, diameter 0.075mm, annealed, 99.9%
Copper, wire reel, 100m, diameter 1.0mm, as drawn, 99.98+%
Copper - O.F.H.C., foil, 20m coil, thickness 0.05mm, coil width 10mm, annealed, 99.95+%
Copper, wire reel, 100m, diameter 1.0mm, annealed, 99.9%
Copper, rod, 200mm, diameter 2.0mm, as drawn, 99.99+%
Copper, sphere, 1000pcs, diameter 3.0mm, precision sphere grade 200
Copper, tube, 100mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%
Sigma-Aldrich
Copper, turnings, purum p.a., ≥99.0%
Sigma-Aldrich
N,N-Dimethylformamide, ACS reagent, ≥99.8%
Sigma-Aldrich
Copper, beads, 2-8 mm, ≥99.99% trace metals basis
Sigma-Aldrich
Copper, foil, ≥99.8% (complexometric)
Supelco
N,N-Dimethylformamide, analytical standard