REACTIONS WITH α, β-SPIROEPOXY-ALKANONES. PART I. SYNTHESIS AND REACTIONS OF OXASPIRO(2,5)OCTA-4-ONES

Abstract

2-Aryl-1-oxaspiro(2,5)octa-4-ones Ia,b were synthesized and reacted with thiourea in ethanol to give hydroxy cyclohexanone derivatives IIa,b. Compounds IIa,b were readily cyclised into the corresponding 5-hydroxy quinazolines IIIa,b and their dehydrated derivatives IVa,b. A mixture of compounds III and IV were also prepared directly from the reaction of compounds Ia,b with thiourea in alkaline medium. Compounds Va,b were produced by reduction of corresponding IV. Compounds III or and V reacted with chloroacetic acid to give resp. VI and VII, which condensed with aromatic aldehydes to form resp. VIII and IX.