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

357456

Sigma-Aldrich

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

349178

Sigma-Aldrich

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

BCR017B

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

IRMM522A

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

IRMM522C

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

BCR054R

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

223409

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

203122

Sigma-Aldrich

Copper, powder, 99.99% trace metals basis

266086

Sigma-Aldrich

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

311405

Sigma-Aldrich

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

326453

Sigma-Aldrich

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

1601500

USP

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

GF96112762

Copper - O.F.H.C., wire reel, 100m, diameter 1.0mm, as drawn, 99.95+%

GF63314827

Copper - O.F.H.C., wire reel, 5m, diameter 0.80mm, as drawn, 99.95+%

GF00803102

Copper - O.F.H.C., sheet, 150x150mm, thickness 12.7mm, 99.99+%

GF86247524

Copper - O.F.H.C., foil, light tested, 100x100mm, thickness 0.025mm, hard, 99.95+%

GF17753340

Copper - O.F.H.C., rod, 200mm, diameter 63.5mm, as drawn, 99.95+%

GF65515451

Copper - O.F.H.C., rod, 1000mm, diameter 38.1mm, as drawn, 99.95+%

GF83569540

Copper - O.F.H.C., tube, 100mm, outside diameter 4.0mm, inside diameter 3mm, wall thickness 0.5mm, 99.95+%

GF46192563

Copper - O.F.H.C., tube, 200mm, outside diameter 4.0mm, inside diameter 3mm, wall thickness 0.5mm, 99.95+%

GF37052041

Copper - O.F.H.C., sheet, 300x300mm, thickness 4.76mm, 99.95+%

GF34111257

Copper - O.F.H.C., tube, 200mm, outside diameter 2.54mm, inside diameter 1.54mm, wall thickness 0.5mm, 99.95+%

GF53898766

Copper - O.F.H.C., rod, 500mm, diameter 25.4mm, as drawn, 99.95+%

GF24203607

Copper - O.F.H.C., sheet, 150x150mm, thickness 12.7mm, 99.95+%

GF99468769

Copper - O.F.H.C., tube, 200mm, outside diameter 10mm, inside diameter 8mm, wall thickness 1.0mm, 99.95+%

GF12566921

Copper - O.F.H.C., tube, 500mm, outside diameter 9.5mm, inside diameter 7.9mm, wall thickness 0.8mm, 99.95+%

GF28440749

Copper - O.F.H.C., sheet, 300x300mm, thickness 6.35mm, 99.95+%

GF24459273

Copper - O.F.H.C., tube, 500mm, outside diameter 1.23mm, inside diameter 0.51mm, wall thickness 0.36mm, 99.95+%

GF61521320

Copper - O.F.H.C., sheet, 50x50mm, thickness 6.35mm, 99.95+%

GF64852331

Copper - O.F.H.C., wire reel, 50m, diameter 0.25mm, as drawn, 99.95+%