A simple, rapid and mild one pot synthesis of benzene ring acylated and demethylated analogues of harmine under solvent-free conditions

Sabira Begum, Syed Nawazish Ali, Farhat, Syed Imran Hassan, Bina S. Siddiqui

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1584-1598
Number of pages15
JournalMolecules
Volume13
Issue number8
DOIs
Publication statusPublished - Aug 2008

Fingerprint

Harmine
Anhydrides
Benzene
benzene
anhydrides
analogs
Acids
halides
rings
synthesis
products
Chromatography
Column chromatography
acids
chromatography
Temperature
room temperature

Keywords

  • β-carboline
  • Acylharmine
  • Demethylation
  • Friedel-crafts acylation
  • Harmine
  • Solvent-free reactions

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A simple, rapid and mild one pot synthesis of benzene ring acylated and demethylated analogues of harmine under solvent-free conditions. / Begum, Sabira; Ali, Syed Nawazish; Farhat, ; Hassan, Syed Imran; Siddiqui, Bina S.

In: Molecules, Vol. 13, No. 8, 08.2008, p. 1584-1598.

Research output: Contribution to journalArticle

Begum, Sabira ; Ali, Syed Nawazish ; Farhat, ; Hassan, Syed Imran ; Siddiqui, Bina S. / A simple, rapid and mild one pot synthesis of benzene ring acylated and demethylated analogues of harmine under solvent-free conditions. In: Molecules. 2008 ; Vol. 13, No. 8. pp. 1584-1598.
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