1,3-Dipolar Cycloaddition of Nitrones with 5-Methylenehydantoins: Synthesis and Transformation of New Spirohydantoin Derivatives

Abstract

1,3-Dipolar cycloaddition of various acyclic nitrones with 5-methylenehydantoin derivatives afforded new chiral spiroadducts in good yields. All the spirohydantoins were obtained through a regio- and stereospecific pathway, and the spirocarbon atom was linked to the isoxazolidine oxygen atom. A representative example of the reduction of the spirohydantoin 8 with Zn/AcOH led to the substituted 1,3-aminoalcohol hydantoin 20.

Keywords:

• 1,3-Dipolar cycloaddition
• 5-methylenehydantoins
• nitrones
• regioselectivity
• stereoselectivity

ACKNOWLEDGMENT

The authors are grateful to DGRSRT (Direction Générale de la Recherche Scientifique et de la Rénovation Technologique) of the Tunisian Ministry of Higher Education, Scientific Research, and Technology for the financial support.

Notes

^a Reaction in toluene at 80 °C for 6 days.

^b Yield of pure 8–19.