An intramolecular Diels–Alder reaction in the synthesis of N-aroyl-3a,6-epoxyisoindole-2-carbothioamides

(Figure presented.) The reaction of allyl(furfuryl)amines with aroyl isothiocyanates was studied. The reaction proceeded via an initial nucleophilic addition of the allylamine nitrogen atom to isothiocyanates and a subsequent spontaneous intramolecular Diels–Alder reaction involving the furan ring of intermediate N-allyl-N-furfurylthioureas with the formation of a single diastereomer of 3a,6-epoxyisoindoles. © 2025 Elsevier B.V., All rights reserved.