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 language | English |
---|---|
Pages (from-to) | 1584-1598 |
Number of pages | 15 |
Journal | Molecules |
Volume | 13 |
Issue number | 8 |
DOIs | |
Publication status | Published - Aug 2008 |
Externally published | Yes |
Keywords
- Acylharmine
- Demethylation
- Friedel-crafts acylation
- Harmine
- Solvent-free reactions
- β-carboline
ASJC Scopus subject areas
- Analytical Chemistry
- Chemistry (miscellaneous)
- Molecular Medicine
- Pharmaceutical Science
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry