6982-75-8

Upstream product

• 625-84-3 2,5-Dimethylpyrrole 
• 102651-96-7 dimethoxy(phenyl)carbenium tetrafluoroborate 
• 98-88-4 benzoyl chloride 
• 60-29-7 diethyl ether 

Downstream Products

• 643744-27-8 (2,5-dimethyl-1-pentyl-1H-pyrrol-3-yl)-phenyl-methanone 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of a series of pyrrole cannabinoid receptor agonists

We designed and synthesized a series of pyrrole derivatives with the aim of investigating the structure-activity relationship (SAR) for the binding of non-classical agonists to CB1 and CB2 cannabinoid receptors. Superposition of two pyrrole-containing cannabinoid agonists, JWH-007 and JWH-161, allowed us to identify positions 1, 3 and 4 of the pyrrole nucleus as amenable to additional investigation. We prepared the 1-alkyl-2,5-dimethyl-3,4-substituted pyrroles 10a-e, 11a-d, 17, 21, 25 and the tetrahydroindole 15, and evaluated their ability to bind to and activate cannabinoid receptors. Noteworthy in this set of compounds are the 4-bromopyrrole 11a, which has an affinity for CB1 and CB2 receptors comparable to that of well-characterized heterocyclic cannabimimetics such as Win-55,212-2; the amide 25, which, although possessing a moderate affinity for cannabinoid receptors, demonstrates that the 3-naphthoyl group, commonly present in indole and pyrrole cannabimimetics, can be substituted by alternative moieties; and compounds 10d, 11d, showing CB1 partial agonist properties.

First Reactions of Dialkoxycarbenium Tetrafluoroborates with Pyrroles, 5H-Dibenzazepines, and Electron-Rich Arenes

Pyrrole (2a) and 2,5-dimethylpyrrole (2b) react with the dialkoxycarbenium tetrafluoroborates 1a-1c under kinetic control to yield the corresponding acylpyrrole derivatives. 5H-Dibenzazepine (9a) and the 10,11-dihydro derivative 9b react only with the most elecrophilic of the series of electrophiles tested, namely, diethoxycarbenium tetrafluoroborate (1a), to furnish the corresponding formyl derivatives.Similarly, in arene chemistry, the highly electron-rich N,N-dimethylaniline (13a) and 1,3,5-trimethoxybenzene (13b) are formylated by reaction with 1a.