Microwave-Assisted Copper Powder-Catalyzed Synthesis of Azole-Fused Pyrimidinones

Author(s): Pham Duy Quang Dao, Chan Sik Cho*, Son Long Ho, Ho-Sang Sohn.

Journal Name: Current Organic Chemistry

Volume 22 , Issue 1 , 2018

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Abstract:

Background: Azole-fused pyrimidinones have been synthesized and tested for biological activities. The present copper-catalyzed version will be attempted as an alternative synthetic method for such N-fused hybrid structures.

Objective: This research aims to develop a new synthetic method of azole-fused pyrimidinones from β-bromo-α,β-unsaturated amides and azoles (benzimidazole, imidazole and pyrazole).

Method: β-Bromo-α,β-unsaturated amides react with azoles in DMF at 100°C for 1 h in the presence of a catalytic amount of copper powder and base under microwave irradiation.

Result: β-Bromo-α,β-unsaturated amides are coupled and cyclized with azoles to give the corresponding azolefused pyrimidinones in moderate to good yields via tandem intermolecular C-N coupling and C-N formative cyclization by C-H activation.

Conclusion: This work provides a new method for synthesizing N-fused hybrid scaffolds such as benzimidazo[ 1,2-a]pyrimidin-2-ones, imidazo[1,2-a]pyrimidinones and pyrazolo[1,5-a]pyrimidinones from readily available starting compounds.

Keywords: Benzimidazole, β-bromo-α, β-unsaturated amide, copper powder, imidazole, pyrazole, pyrimidinone.

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Article Details

VOLUME: 22
ISSUE: 1
Year: 2018
Page: [85 - 93]
Pages: 9
DOI: 10.2174/1385272821666170531122318

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