INTRAMOLECULAR DIELS–ALDER REACTION IN THE SYNTHESIS OF 5-ARYLISOXAZOLYLMETHYL- AND 4,5-DICHLOROISOTHIAZOLYLMETHYL-3a,6-EPOXYISOINDOL-3-ONES

Abstract

The reaction of 5-arylisoxazolyl- and 4,5-dichloroisothiazolylallylamines with pyromucic acid chlorides (2-furoyl and 5-methyl-2furoyl chlorides) was studied. The reaction proceeds via the initial acylation of the allylamine nitrogen atom and the subsequent spontaneous intramolecular Diels–Alder reaction involving the furan ring of intermediate N-furoylamides with the formation of a single diastereomer of 3a,6-epoxyisoindol-3-ones.