Cycloaddition of dichloroketene to N,N-disubstituted 3-aminomethylene-5-hydroxy-2,2-dimethyl-7-pentyl-4-chromanone: synthesis of 2H,5H-pyrano[3,2-c][1]benzopyran derivatives.
The synthesis of N,N-disubstituted 3-aminomethylene-5-hydroxy-2,2-dimethyl-7-pentyl-4-chromanones (III) and their reaction with dichloroketene are described. The resulting cycloadducts (IV) gave, by dehydrochlorination, the N,N-disubstituted 4-amino-3-chloro-10-hydroxy-5,5-dimethyl-8-pentyl-2H,5H-pyrano[3,2-c] [1]benzopyran-2-ones (V), which are structurally related to tetrahydrocannabinols. Only the compound (V a) displayed a very weak stimulant activity on the CNS.
D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D001921:Brain / Q000187:drug effects*; D000697:Central Nervous System Stimulants / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D002839:Chromans; D004000:Dichloroethylenes; D051379:Mice
D001578:Benzopyrans; D000697:Central Nervous System Stimulants; D002839:Chromans; D004000:Dichloroethylenes; C039586:dichloroketene