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

ABSTRAKT

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.

MATERIAŁY

Numer produktu

Marka

Opis produktu

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

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%

311405

Sigma-Aldrich

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

326453

Sigma-Aldrich

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

203122

Sigma-Aldrich

Copper, powder, 99.99% trace metals basis

BCR017B

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

1601500

USP

Rozpuszczalnik resztkowy klasy 2 - N,N-dimetyloformamid, United States Pharmacopeia (USP) Reference Standard

GF11778004

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

GF88633963

Copper - O.F.H.C., tube, 100mm, outside diameter 9.5mm, inside diameter 7.9mm, wall thickness 0.8mm, 99.95+%

GF12392894

Copper - O.F.H.C., wire reel, 10m, diameter 0.80mm, as drawn, 99.95+%

GF90524820

Copper - O.F.H.C., tube, 100mm, outside diameter 0.635mm, inside diameter 0.275mm, wall thickness 0.18mm, 99.95+%

GF46192563

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

GF24040516

Copper - O.F.H.C., wire reel, 2m, diameter 2.0mm, hard, 99.95+%

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%

GF54651146

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

GF41333273

Copper, tube, 100mm, outside diameter 1.5mm, inside diameter 0.6mm, wall thickness 0.45mm, as drawn, 99.9%

GF22027799

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

GF67220298

Copper - O.F.H.C., foil, 2m coil, thickness 0.25mm, half hard, 99.95+%

GF35866761

Copper, tube, 200mm, outside diameter 10.4mm, inside diameter 10mm, wall thickness 0.2mm, as drawn, 99.9%

GF10347746

Copper, wire reel, 0.1m, diameter 0.1mm, aluminum cladding, outside diameter 0.25mm, 99.9%

GF43015430

Copper - O.F.H.C., foil, 6mm disks, thickness 0.025mm, hard, 99.95+%

GF71667366

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

GF20964427

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

GF01344518

Copper - O.F.H.C., foil, 50mm disks, thickness 0.7mm, half hard, 99.95+%