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Synthesis and spectroscopic characterization of cyclobutyl hydantoins

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Abstract The hydantoin moiety has proved to be an important pharmacophore that confers a wide range of biological properties to different derivatives. Thus, synthetic methods have been developed to obtain… Click to show full abstract

Abstract The hydantoin moiety has proved to be an important pharmacophore that confers a wide range of biological properties to different derivatives. Thus, synthetic methods have been developed to obtain such molecules. Herein, we describe the heterocyclization process to obtain imidazolidine-2,4-diones (hydantoin compounds) from methylcyclobutyl ketones and cyclobutanones derived from (−)-(1S)-α-pinene and (−)-(1S)-verbenone through the Bucherer-Berg reaction. The methylcyclobutyl hydantoins and the spirohydantoin obtained were fully characterized, determining their absolute stereochemistry by nuclear magnetic resonance experiments and theoretical calculations.

Keywords: spectroscopic characterization; synthesis spectroscopic; characterization cyclobutyl; cyclobutyl hydantoins

Journal Title: Journal of Molecular Structure
Year Published: 2018

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