Synthesis and spectroscopic characterization of cyclobutyl hydantoins

CATURELLI, JUAN; MARTINI, M. FLORENCIA; FABIAN, LUCAS; MOLTRASIO, GRACIELA Y.; MOGLIONI, ALBERTINA G.

JOURNAL OF MOLECULAR STRUCTURE

ELSEVIER SCIENCE BV

Año: 2018

0022-2860

The hydantoin moiety has proved to be an important pharmacophore that confers a widerange 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)--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.