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

07-4430

Sigma-Aldrich

N,N-Dimethylformamide, JIS special grade, ≥99.5%

07-4440

Sigma-Aldrich

N,N-Dimethylformamide, SAJ first grade, ≥99.0%

648531

Sigma-Aldrich

N,N-Dimethylformamide, suitable for HPLC, ≥99.9%

BCR058

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

227056

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

72438

Supelco

N,N-Dimethylformamide, analytical standard

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

437573

Sigma-Aldrich

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

326488

Sigma-Aldrich

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

349208

Sigma-Aldrich

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349216

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

349151

Sigma-Aldrich

Copper, foil, thickness 0.5 mm, 99.98% trace metals basis

349224

Sigma-Aldrich

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

326410

Sigma-Aldrich

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

254177

Sigma-Aldrich

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

266744

Sigma-Aldrich

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

326429

Sigma-Aldrich

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

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

GF97882835

Copper - O.F.H.C., sheet, 100x100mm, thickness 4.76mm, 99.95+%

GF33500607

Copper - O.F.H.C., rod, 200mm, diameter 50.0mm, as drawn, 99.95+%

GF27357240

Copper - O.F.H.C., foil, light tested, 25x25mm, thickness 0.075mm, half hard, 99.95+%

GF58595675

Copper - O.F.H.C., tube, 200mm, outside diameter 1.23mm, inside diameter 0.51mm, wall thickness 0.36mm, 99.95+%

GF93325642

Copper - O.F.H.C., tube, 100mm, outside diameter 3.2mm, inside diameter 2.4mm, wall thickness 0.4mm, 99.95+%

GF51452300

Copper - O.F.H.C., foil, 6mm disks, thickness 0.7mm, half hard, 99.95+%

GF39253721

Copper - O.F.H.C., sheet, 50x50mm, thickness 4.76mm, 99.95+%

GF50461927

Copper - O.F.H.C., tube, 500mm, outside diameter 0.635mm, inside diameter 0.275mm, wall thickness 0.18mm, 99.95+%

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Copper - O.F.H.C., wire reel, 10m, diameter 0.125mm, annealed, 99.95+%

GF41581335

Copper - O.F.H.C., foil, 100x100mm, thickness 0.25mm, annealed, 99.95+%

GF96885905

Copper - O.F.H.C., rod, 100mm, diameter 16mm, as drawn, 99.95+%