A simple, rapid and mild one pot synthesis of benzene ring acylated and demethylated analogues of harmine under solvent-free conditions.
A simple, rapid, solvent-free, room temperature one pot synthesis of benzene ring acylated and demethylated analogues of harmine using acyl halides/acid anhydrides and AlCl(3) has been developed. Eight different acyl halides/acid anhydrides were used in the synthesis. The resulting mixture of products was separated by column chromatography to afford 10- and 12-monoacyl analogues, along with 10,12-diacyl-11-hydroxy products. In five cases the corresponding 10-acyl-11-hydroxy analogues were also obtained. Yields from the eight syntheses (29 products in total) were in the 6-34% range and all compounds were fully characterized.
Begum
Sabira
S
H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan. sabira@khi.comsats.net.pk
Ali
Syed Nawazish
SN
Farhat
Hassan
Syed Imran
SI
Siddiqui
Bina S
BS
D000107:Acetylation; D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry; D001554:Benzene / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry; D006247:Harmine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D026121:Indole Alkaloids; D008745:Methylation
D017607:Aluminum Compounds; D000812:Anhydrides; D002712:Chlorides; D026121:Indole Alkaloids; D000077410:Aluminum Chloride; D006247:Harmine; D001554:Benzene
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