Allylation of Ketones with Methyl 3-(Bromomethyl)but-3-enoate. Synthesis of Bioactive Unsaturated Lactones Based on Benzo[f]coumarin and Its Derivatives.

Lamekina, Yu. P.; Kulahava, T. A.; Shumski, V. A.; Mineyeva, I. V.

Efficient procedures have been developed for the allylation of structurally diverse ketones with methyl 3-(bromomethyl)but-3-enoates, and the possibility of using the allylation products in the target-oriented synthesis of new heterocyclic compounds has been demonstrated. Modification of benzo[f]coumarin derivatives at the keto group via Barbier allylation with methyl 3-(bromomethyl)but-3-enoate has been performed for the first time with the goal of subsequent formation of a lactone fragment. The synthesized benzo[f]coumarin derivatives have been characterized by spectral methods, and their ability to penetrate phospholipid bilayer has been estimated. These compounds have been found to affect neither viability nor proliferation of C6 rat glioma cells. The obtained benzo[f]coumarin derivatives exhibit antioxidant properties in model systems based on hydrogen peroxide and sodium hypochlorite.

COUMARIN derivatives; METHYL ketones; COUMARINS; ALLYLATION; HETEROCYCLIC compounds synthesis; LACTONES

Russian Journal of Organic Chemistry, 2022, Vol 58, Issue 6, p751

1070-4280

Academic Journal

10.1134/S1070428022060021