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

270547

Sigma-Aldrich

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

227056

Sigma-Aldrich

N,N-Dimethylformamide, anhydrous, 99.8%

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72438

Supelco

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

326488

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254177

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266744

Sigma-Aldrich

Copper, foil, thickness 1.0 mm, 99.999% trace metals basis

207780

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349151

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349216

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Copper, wire, diam. 1.0 mm, ≥99.9%

326429

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349208

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61139

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Copper, turnings, purum p.a., ≥99.0%

349224

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1601500

USP

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

326410

Sigma-Aldrich

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494488

Sigma-Aldrich

N,N-Dimethylformamide, biotech. grade, ≥99.9%

33120

Sigma-Aldrich

N,N-Dimethylformamide, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.8% (GC)

D158550

Sigma-Aldrich

N,N-Dimethylformamide, ReagentPlus^®, ≥99%

319937

Sigma-Aldrich

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

GF60058346

Copper, sphere, 1000pcs, diameter 3.0mm, precision sphere grade 200

GF53474980

Copper, tube, 100mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF98886920

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

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%

GF69447280

Copper, tube, 100mm, outside diameter 0.75mm, inside diameter 0.23mm, wall thickness 0.26mm, as drawn, 99.9%

GF77355579

Copper, tube, 1000mm, outside diameter 0.65mm, inside diameter 0.21mm, wall thickness 0.22mm, as drawn, 99.9%