Reactivity of N‐Substituted Exo‐oxazolidin‐2‐one Dienes with Naphthalene Chalcones and Cyclic 1,3‐Dicarbonyl Compounds.

The N‐substituted exo‐2‐oxazolidinone dienes are versatile molecules that undergo a variety of reactions. To further explore this versatility, Diels‐Alder reactions were carried out with novel naphthalene chalcones. Upon attempting the Diels‐Alder reaction with 2‐hydroxy‐1,4‐naphthoquinone, the formation of chromene unexpectedly took place via a formal [3+3] cycloaddition reaction. The observed reaction was then achieved with other 1,3‐dicarbonyl compounds. Cycloaddition Tales: Versatile N‐substituted exo‐2‐oxazolidinone dienes underwent different cycloaddition reactions, including the famous Diels‐Alder reaction, with novel chalcones to synthesize benzoxazole‐2‐ones and [3+3] formal cycloaddition with 1,3‐dicarbonyl compounds to synthesize chromenes. Both displayed interesting regio‐ and diastereoselectivity. [ABSTRACT FROM AUTHOR]