期刊
TETRAHEDRON LETTERS
卷 55, 期 4, 页码 842-844出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.12.021
关键词
1-(3-Oxo)ureas; Curtius rearrangement; Carbamoylcarbamate; gamma-Keto carboxylic acid; 1-(3-Oxocyclobutyl) carboxylic acid
资金
- Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy
- NIDA [Y1-DA1101]
- Naval Research Laboratory (NRL)
1-(3-Oxocyclobutyl) carboxylic acid (4a) was converted into N-Boc-protected 1-(3-oxocyclobutyl) urea (5a), a key intermediate for the preparation of agonists of metabotropic glutamate receptor 5, in one-step when treated with diphenyl phosphoryl azide and triethylamine in tert-butanol. The mechanism of the reaction involves a nucleophilic addition of the in situ generated tert-butyl carbamate to the isocyanate intermediate. This reaction is applicable to other 1-(3-oxocycloalkyl) carboxylic acids but not to linear gamma-keto carboxylic acids. (C) 2014 Published by Elsevier Ltd.
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