Copper-Mediated Synthesis of Aryl α-Keto Amides from Epoxide Derivatives

Fenghua Liu; Yunjian Cui; Yi Dong; Heng Xu

doi:10.1055/s-0040-1707990

Synlett, Table of Contents

Synlett 2020; 31(10): 1011-1014
DOI: 10.1055/s-0040-1707990

letter

Copper-Mediated Synthesis of Aryl α-Keto Amides from Epoxide Derivatives

Authors

Fenghua Liu ◊

^aSchool of Pharmacy, Jiamusi University, Jiamusi 154007, P. R. of China
Yunjian Cui ◊

^aSchool of Pharmacy, Jiamusi University, Jiamusi 154007, P. R. of China
Yi Dong

^bBeijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China Email: xuheng@imm.ac.cn
Heng Xu ∗

^bBeijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China Email: xuheng@imm.ac.cn

Abstract

All articles of this category

^◊ These authors contributed equally.

Abstract

A novel Cu^II-mediated synthesis of aryl α-keto amides from epoxide derivatives is reported. This transformation was conducted by using O₂ as a green oxidant that meets the requirements of sustainable chemistry.

Key words

copper catalysis - keto amides - epoxides - green chemistry

Full Text

References

References and Notes
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10 α-Keto Amides 3a–l; General Procedure A mixture of the appropriate epoxide 1 (1.0 mmol) and Cu(OAc)₂ (2.0 mmol) in DMF (2.0 mL) was stirred overnight at 120 °C under O₂, then cooled to r.t. and diluted with EtOAc. H₂O was added, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried (Na₂SO₄), and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel). N,N-Dimethyl-2-oxo-2-phenylacetamide (3a) Colorless oil; yield: 133 mg (75%), R_f = 0.5 (EtOAc–PE, 1:3). ¹H NMR (400 MHz, CDCl₃): δ = 8.12–7.84 (m, 2 H), 7.72–7.57 (m, 1 H), 7.57–7.41 (m, 2 H), 3.08 (s, 3 H), 2.93 (s, 3 H). ¹³C NMR (101 MHz, CDCl₃): δ = 191.9, 167.2, 134.9, 133.2, 129.8, 129.1, 37.2, 34.1. N,N-Dimethyl-2-oxo-2-(4-tolyl)acetamide (3b) Colorless oil; yield: 124 mg (65%); R_f = 0.5 (EtOAc–PE, 1:3). ¹H NMR (400 MHz, CDCl₃): δ = 7.79 (d, J = 8.2 Hz, 2 H), 7.26 (d, J = 7.9 Hz, 2 H), 3.06 (s, 3 H), 2.90 (s, 3 H), 2.39 (s, 3 H). ¹³C NMR (101 MHz, CDCl₃): δ = 191.7, 167.4, 146.1, 130.8, 130.0, 129.9, 37.2, 34.1, 22.0.

Supplementary Material

Supporting Information (PDF)