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Synthesis 2015; 47(01): 108-112
DOI: 10.1055/s-0034-1379104
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Alcoholysis of 3-Iodopropynamides: Selective Synthesis of Carbamoylacetates

Jian-Sheng Tang
a   College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +86(731)88821488   Email: ccguo@hnu.edu.cn
b   Laboratory of Organic Chemistry, Hunan First Normal University, Changsha 410205, P. R. of China
,
Can-Cheng Guo*
a   College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +86(731)88821488   Email: ccguo@hnu.edu.cn
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Publication History

Received: 10 July 2014

Accepted after revision: 15 August 2014

Publication Date:
25 September 2014 (online)

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Abstract

A novel and selective method for the synthesis of carbamoylacetates via the alcoholysis of 3-iodopropynamides has been developed. 3-Iodopropynamides react with alcohols in the presence of palladium(II) acetate and DABCO to afford the corresponding carbamoylacetates in moderate to good yields.

Key words

palladium - 1,4-diazabicyclo[2.2.2]octane - alcoholysis - 3-iodopropynamides - carbamoylacetates

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