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

BCR058

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

227056

Sigma-Aldrich

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72438

Supelco

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12816

Sigma-Aldrich

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326488

Sigma-Aldrich

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349208

Sigma-Aldrich

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349216

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349151

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349224

Sigma-Aldrich

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326410

Sigma-Aldrich

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254177

Sigma-Aldrich

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266744

Sigma-Aldrich

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326429

Sigma-Aldrich

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207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

61139

Sigma-Aldrich

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D4551

Sigma-Aldrich

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270547

Sigma-Aldrich

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

GF00529040

Copper, sphere, 100pcs, diameter 3.0mm, precision sphere grade 200

GF23864463

Copper, tube, 1000mm, outside diameter 0.75mm, inside diameter 0.23mm, wall thickness 0.26mm, as drawn, 99.9%

GF93436926

Copper, tube, 1000mm, outside diameter 0.95mm, inside diameter 0.29mm, wall thickness 0.33mm, as drawn, 99.9%

GF92323166

Copper, microfoil, disks, 25mm, thinness 0.25μm, specific density 219.9μg/cm², permanent mylar 3.5μm support, 99.99+%

GF27429891

Copper, rod, 100mm, diameter 6.35mm, as drawn, 99.999%

GF98886920

Copper, rod, 50mm, diameter 12.7mm, as drawn, 99.99+%

GF13846877

Copper, rod, 100mm, diameter 16mm, as drawn, 99.99+%

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