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

1601500

USP

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

BCR017B

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

IRMM522A

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

203122

Sigma-Aldrich

Copper, powder, 99.999% trace metals basis

BCR054R

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

311405

Sigma-Aldrich

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

326453

Sigma-Aldrich

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

223409

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

357456

Sigma-Aldrich

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

266086

Sigma-Aldrich

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

349178

Sigma-Aldrich

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

GF47295603

Copper - O.F.H.C., foil, 8mm disks, thickness 0.125mm, hard, 99.95+%

GF15696243

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

GF55729468

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

GF22788580

Copper - O.F.H.C., tube, 200mm, outside diameter 1.78mm, inside diameter 0.8mm, wall thickness 0.49mm, 99.95+%

GF15996224

Copper - O.F.H.C., foil, 8mm disks, thickness 0.7mm, half hard, 99.95+%

GF30268076

Copper - O.F.H.C., tube, 1000mm, outside diameter 9.5mm, inside diameter 7.9mm, wall thickness 0.8mm, 99.95+%

GF11778004

Copper - O.F.H.C., foil, light tested, 150x150mm, thickness 0.075mm, half hard, 99.95+%

GF51455459

Copper, tube, 1000mm, outside diameter 3.0mm, inside diameter 1.2mm, wall thickness 0.9mm, as drawn, 99.9%

GF54025792

Copper, tube, 100mm, outside diameter 1.2mm, inside diameter 0.56mm, wall thickness 0.32mm, as drawn, 99.9%

GF76135631

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

GF22915436

Copper, tube, 1000mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, as drawn, 99.9%

GF31651455

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

GF54651146

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

GF84281935

Copper, tube, 100mm, outside diameter 0.25mm, inside diameter 0.05mm, wall thickness 0.1mm, as drawn, 99.9%

GF19533090

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

GF22027799

Copper, tube, 1000mm, outside diameter 6.35mm, inside diameter 4.93mm, wall thickness 0.71mm, as drawn, 99.9%

GF14973060

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

GF29372441

Copper, sphere, 100pcs, diameter 1.0mm, precision sphere grade 200

GF16408425

Copper, tube, 1000mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%