Original scientific paper

Preparation and Cyclization of Some B-Keto-Y-Phthalimidoaliphatic Esters

N. Bregant ; Laboratory of Organic Chemistry and Biochemi stry, Facuity of Science, and Institute of Organic Chemistry and Biochemistry, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia
A. Nuri ; Laboratory of Organic Chemistry and Biochemi stry, Facuity of Science, and Institute of Organic Chemistry and Biochemistry, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia
M. Štromar ; Laboratory of Organic Chemistry and Biochemi stry, Facuity of Science, and Institute of Organic Chemistry and Biochemistry, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia

Abstract

The preparation of (a.-phthalimidoacyl)malonates via mixed
anhydrides (Ila, b) and subsequent monodeethoxycarbonylation into
the (a.-phthalimidoacyl)acetates (IVa, b) is described. Cyclization ·of
(Illa) with hydroxylamine led to 3-(phthalimidomethyl)isoxazolin-
5-one-4-carboxylic acid (VI), while the malonate derivative (IIIb),
when reacted with hydrazine, gave 4-ethoxycarbonyl-3-(a.-phthalimidoethyl) pyrazolin-5-one (VII). The ketalization of ethyl (phthalimidoacetyl) acetate (!Va) with methyl orthoformate gave methyl
(phthalimidoacetyl)acetate dimethyl ketal (V). The structure of the
obtained compounds is discussed on the basis of their 1H nuclear
magnetic resonance spectra, in some cases supported by infrared
data.

Keywords

Hrčak ID:

196579

URI

https://hrcak.srce.hr/196579

Publication date:

16.2.1976.

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