Synthesis of Tri- and Tetracycle Compounds via Reaction of 1,3-Decalinediones and 4-Hydroxycoumarines with 2-Acetyl-2-Cyclohexenes and Biological Testing

Abstract

2-Acetyl-5, 5-dimethyl-2-cyclohexen-l-one reacts with decalin-1,3-dions (9a, b) and 4-hydroxycoumarins (13a, b) following the pattern of a Michael addition with the formation of tricyclic compounds (10a, b and 14a, b). In the case of unsubstituted 2-acetyl-2-cyclohexen-l-one reaction with 4-hydroxycoumarine follows pattern of a DieIs-Alder heterodiene condensation to form tetracycle (15). Dehydration of both types of adduct gives tetracyclic compounds (11a, b and 16a, b, c). Coumarine derivatives (14a, b, 15, 16c) were tested for anticoagulative activity.