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A Simple, Rapid and Mild One Pot Synthesis of Benzene Ring Acylated and Demethylated Analogues of Harmine under Solvent-free Conditions

Author(s): Sabira Begum | Syed Nawazish Ali | Farhat Farhat | Syed Imran Hassan | Bina S. Siddiqui

Journal: Molecules
ISSN 1420-3049

Volume: 13;
Issue: 8;
Start page: 1584;
Date: 2008;
Original page

Keywords: Solvent-free reactions | Friedel-Crafts acylation | β-carboline | harmine | acylharmine | demethylation.

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 AlCl3 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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