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

349178

Sigma-Aldrich

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

1601500

USP

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

326453

Sigma-Aldrich

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

223409

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

203122

Sigma-Aldrich

Copper, powder, 99.999% trace metals basis

IRMM522C

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

IRMM522A

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

311405

Sigma-Aldrich

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

BCR054R

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

266086

Sigma-Aldrich

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

357456

Sigma-Aldrich

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

BCR017B

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

GF19533090

Copper, tube, 1000mm, outside diameter 1.75mm, inside diameter 0.33mm, wall thickness 0.71mm, as drawn, 99.9%

GF76135631

Copper, rod, 50mm, diameter 5.0mm, as drawn, 99.999%

GF14973060

Copper, tube, 100mm, outside diameter 10.4mm, inside diameter 10mm, wall thickness 0.2mm, as drawn, 99.9%

GF54651146

Copper, tube, 1000mm, outside diameter 0.25mm, inside diameter 0.05mm, wall thickness 0.1mm, as drawn, 99.9%

GF31651455

Copper, rod, 50mm, diameter 16mm, as drawn, 99.99+%

GF27350287

Copper, wire reel, 1000m, diameter 0.1mm, annealed, 99.9%

GF02537298

Copper - O.F.H.C., foil, 5m coil, thickness 0.25mm, half hard, 99.95+%

GF15255042

Copper - O.F.H.C., foil, 4mm disks, thickness 0.1mm, hard, 99.95+%

GF90710298

Copper, wire reel, 0.5m, diameter 1.0mm, as drawn, 99.99+%

GF87225813

Copper - O.F.H.C., foil, 50mm disks, thickness 0.006mm, hard, 99.95+%

GF63655780

Copper, wire reel, 1000m, diameter 0.25mm, annealed, 99.9%

GF56973257

Copper, wire reel, 2000m, diameter 0.25mm, annealed, 99.9%

GF39830227

Copper - O.F.H.C., foil, 4mm disks, thickness 0.125mm, hard, 99.95+%

GF90153503

Copper, wire reel, 20m, diameter 0.25mm, annealed, 99.9%

GF48762300

Copper, tube, 500mm, outside diameter 3.5mm, inside diameter 1.56mm, wall thickness 0.97mm, as drawn, 99.9%

GF71667366

Copper, wire reel, 1000m, diameter 0.04mm, annealed, 99.9%

GF14041864

Copper, wire reel, 200m, diameter 0.5mm, as drawn, 99.98+%

GF20964427

Copper - O.F.H.C., foil, 2m coil, thickness 0.075mm, half hard, 99.95+%