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Article

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

H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
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Molecules 2008, 13(8), 1584-1598; https://doi.org/10.3390/molecules1301584
Received: 6 May 2008 / Revised: 24 June 2008 / Accepted: 23 July 2008 / Published: 6 August 2008
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
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. View Full-Text
Keywords: Solvent-free reactions; Friedel-Crafts acylation; β-carboline; harmine; acylharmine; demethylation. Solvent-free reactions; Friedel-Crafts acylation; β-carboline; harmine; acylharmine; demethylation.
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MDPI and ACS Style

Begum, S.; Ali, S.N.; Farhat, F.; Hassan, S.I.; Siddiqui, B.S. A Simple, Rapid and Mild One Pot Synthesis of Benzene Ring Acylated and Demethylated Analogues of Harmine under Solvent-free Conditions. Molecules 2008, 13, 1584-1598. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules1301584

AMA Style

Begum S, Ali SN, Farhat F, Hassan SI, Siddiqui BS. A Simple, Rapid and Mild One Pot Synthesis of Benzene Ring Acylated and Demethylated Analogues of Harmine under Solvent-free Conditions. Molecules. 2008; 13(8):1584-1598. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules1301584

Chicago/Turabian Style

Begum, Sabira, Syed N. Ali, Farhat Farhat, Syed I. Hassan, and Bina S. Siddiqui 2008. "A Simple, Rapid and Mild One Pot Synthesis of Benzene Ring Acylated and Demethylated Analogues of Harmine under Solvent-free Conditions" Molecules 13, no. 8: 1584-1598. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules1301584

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