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Title: 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. Author: Cafaggi S, Romussi G, Ciarallo G, Bignardi G. Journal: Farmaco Sci; 1983 Oct; 38(10):775-83. PubMed ID: 6139296. Abstract: 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.[Abstract] [Full Text] [Related] [New Search]