Abstract
A simple and novel route for synthesis of new spirocyclic compound is developed. The present work involves condensation of ethyl nipecotate with 2-furaldehyde followed by the MnO2 oxidation to give the β-keto ester which upon reaction with hydrazine hydrate gives the spiro pyrazolone.
Highlights
Spirocyclic compounds have attracted the attention of organic chemists due to their unique structural and reactivity pattern
(3), was prepared by the condensation of 1-tert-butyl 3-ethyl 3-(furan-2-carbonyl)piperidine-1,3dicarboxylate (2) with hydrazine hydrate in acidic medium (Scheme 1)
The intermediate 2 was in turn prepared by the condensation of ethyl nipecotate (1) with furfuraldehyde in presence of lithium diisopropyl amide (LDA) followed by MnO2 oxidation [7,8,9]
Summary
Spirocyclic compounds have attracted the attention of organic chemists due to their unique structural and reactivity pattern. (3), was prepared by the condensation of 1-tert-butyl 3-ethyl 3-(furan-2-carbonyl)piperidine-1,3dicarboxylate (2) with hydrazine hydrate in acidic medium (Scheme 1). The intermediate 2 was in turn prepared by the condensation of ethyl nipecotate (1) with furfuraldehyde in presence of lithium diisopropyl amide (LDA) followed by MnO2 oxidation [7,8,9]. The IR spectrum of compound (3) showed a wide absorption band at 3,412 cm−1 due to the presence of NH in the molecule.
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