Molecules 2008, 13(8), 1584-1598; doi:10.3390/molecules1301584
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
* Author to whom correspondence should be addressed.
Received: 6 May 2008; in revised form: 24 June 2008 / Accepted: 23 July 2008 / Published: 6 August 2008
(This article belongs to the Special Issue Alkaloids)
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Abstract: 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.
Keywords: 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.

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.

Chicago/Turabian Style

Begum, Sabira; Ali, Syed N.; Farhat, Farhat; Hassan, Syed I.; Siddiqui, Bina S. 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.

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