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

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

D4551

Sigma-Aldrich

N,N-Dimethylformamide, for molecular biology, ≥99%

72438

Supelco

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326488

Sigma-Aldrich

Copper, beads, 2-8 mm, ≥99.99% trace metals basis

BCR058

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266744

Sigma-Aldrich

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254177

Sigma-Aldrich

Copper, beads, 2-8 mm, 99.9995% trace metals basis

326410

Sigma-Aldrich

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326429

Sigma-Aldrich

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207780

Sigma-Aldrich

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349208

Sigma-Aldrich

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349224

Sigma-Aldrich

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349151

Sigma-Aldrich

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349216

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

227056

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

319937

Sigma-Aldrich

N,N-Dimethylformamide, ACS reagent, ≥99.8%

33120

Sigma-Aldrich

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GF09445664

Copper - O.F.H.C., foil, light tested, 25x25mm, thickness 0.05mm, hard, 99.95+%

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