New Heterocycles from 8‐Hydroxyquinoline via Dipolar 1,3‐Cycloadditions: Synthesis and Biological Evaluation.

Abstract

Diarylnitrilimine and arylnitriloxide dipoles react with two 8-hydroxyquinoline substrates to give respectively pyrazolinic and isoxazolinic derivatives. The structure of these new heterocycles was established on the basis of their spectroscopic data and by chemical methods. The inhibition activity of one of these heterocycles was evaluated in vitro against 8 pathogenic µ-organisms.

Isomerization of Allylbenzenes

“…Heterocycles bearing allyl groups have also been successfully isomerized. Two examples include the isomerization of 7-allyl-8-aminoisoquinoline and 7-allyl-8-hydroxyisoquinoline, , which when treated with potassium hydroxide in alcohol solvents gave the products 42a and 42b in yields of 90% and 72%, respectively. Finally, 4-allyl-2,3-dihydrobenzofuran-5-ol and 6-allyl-5-methoxy-2,3-dihydrobenzofuran were isomerized under similar conditions to afford 43 and 44 in good yields .…”