Reformatsky Reaction of Methyl α-Bromoisobutyrate with 2-Arylmethylidenemalonic Acid Derivatives

Author: Shchepin V.   Fotin D.  

Publisher: MAIK Nauka/Interperiodica

ISSN: 1070-4280

Source: Russian Journal of Organic Chemistry, Vol.41, Iss.7, 2005-07, pp. : 1011-1015

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Abstract

Reformatsky reagent obtained by treatment of methyl α-bromoisobutyrate with zinc reacts with dimethyl 2-arylmethylidenemalonates to give trimethyl 2-aryl-3-methylbutane-1,1,3-tricarboxylates. The reaction of the same compound with ethyl 3-aryl-2-(4-methylphenylcarbamoyl)acrylates yields cyclic products, ethyl 4-aryl-5,5-dimethyl-1-(4-methylphenyl)-2,6-dioxopiperidine-3-carboxylates. Treatment of the latter with morpholine and phenylhydrazine leads to the corresponding 4-aryl-5,5-dimethyl-1-(4-methylphenyl)-2,6-dioxopiperidine-3-carboxylic acid morpholides and phenylhydrazides. The products are formed as a single diastereoisomer.

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