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 produc...
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Veröffentlicht in: | Molecules (Basel, Switzerland) Switzerland), 2008-08, Vol.13 (8), p.1584-1598 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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. |
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ISSN: | 1420-3049 1420-3049 |
DOI: | 10.3390/molecules1301584 |