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Synthesis 2010(2): 211-216  
DOI: 10.1055/s-0029-1217098
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© Georg Thieme Verlag Stuttgart ˙ New York

Michael Addition-Lactonization Reaction of Electron-Deficient Alkynes with N-(Diphenylmethylene)glycinates: An Efficient Synthesis of 3-Amino-2-pyrone Derivatives

Qing-Fa Zhou, Yong Zhu, Wei-Fang Tang, Tao Lu*
Department of Organic Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. of China
Fax: +86(25)86285179; e-Mail: lut163@163.com;
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Publication History

Received 6 July 2009
Publication Date:
03 November 2009 (online)

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Abstract

A mild and efficient process for the synthesis of 3-amino-2-pyrone derivatives has been developed. This approach is based on the Michael addition of N-(diphenylmethylene)glycinates to various alkynyl ketones, followed by lactonization using 10 mol% sodium hydroxide as catalyst. Aromatic and aliphatic alkynyl ketones were converted into the corresponding 3-amino-2-pyrone derivatives in moderate to high yields. When methyl propiolate was submitted to the reaction, α,β-dehydroamino acids were formed in good yields.

Key words

3-amino-2-pyrone derivatives - alkynyl ketones - Michael addition - lactonization - synthesis