.ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIII. The synthesis and configuration of alkyl 2-acylamino-2-alkenoates and their cyclized 2,5-piperazinedione derivatives.
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概要
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It is described that alkyl (<I>E</I>)- and (<I>Z</I>)-2-halo (Cl, Br, and I)-acetylamino-2-alkenoate (DHA), obtained by the condensation of alkyl 2-oxoalkanoate with chloro- or bromoacetamide and by halogen exchange from the chlorine of DHA to iodine, are cyclized with ammonia or hydroxylamine to give the (<I>E</I>)- and (<I>Z</I>)-isomers of unsymmetric 3-alkylidene-2,5-piperazinediones and their 1-hydroxy derivatives respectively. Alkyl (<I>E</I>)- and (<I>Z</I>)-2-iodoacetylamino-2-alkenoates were converted into the corresponding acetylamino- and phthalimidoacetylamino derivatives. The configurations of all the DHA and 2,5-piperazinedione derivatives were determined from the NMR spectra data.
- 公益社団法人 日本化学会の論文
著者
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Shin Chung-gi
Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University
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Yoshimura Juji
Laboratorium für Organische Chemie Technische Hochschule Tokyo
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Ohtsuka Akira
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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Hayakawa Masato
Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University
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Suzuki Takamichi
Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University
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Shin Chung-gi
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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