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Synthesis 2011(18): 2984-2994  
DOI: 10.1055/s-0030-1260156
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1,2-Diketones from β-Keto Nitriles via a Protection-Oxidative-Decyanation-Deprotection Protocol

Yu Liu, Xiliu Yun, Daisy Zhang-Negrerie, Jianhui Huang, Yunfei Du*, Kang Zhao*
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
Fax: +86(22)27404031; e-Mail: duyunfeier@tju.edu.cn; e-Mail: kangzhao@tju.edu.cn;
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Publication History

Received 29 May 2011
Publication Date:
05 August 2011 (online)

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Abstract

A variety of 1,2-diketones were prepared from β-keto nitriles via a three-step protocol including the protection of the ketones with methoxyamine, oxidative decyanation, and microwave-assisted deprotection in the final step. This approach provides a novel and efficient access to a wide scope of symmetric and unsymmetric 1,2-diketones using molecular oxygen as the oxidant in the decyanation process.

Key words

β-keto nitriles - oxygen - oxidative decyanation - microwave - 1,2-diketones

31

Moran observed that the Z-isomer of 3d was completely converted into the E-isomer in CDCl3 at r.t. after a few days. For details, see ref. 28b. We also found the existence of both Z- and E-isomers in the crude mixture of 3a-j, but the mixture turned into a single isomer in CDCl3 at r.t. after some time.