944443-33-8

Usage

Structure

Quinuclidinone derivative with a benzodioxol ring

Potential pharmacological properties

Therapeutic agent for the treatment of various medical conditions

Use

Building block in the synthesis of various pharmaceutical compounds

Significance

Unique structure and potential applications in drug discovery and development.

Upstream product

• 3731-38-2 3-Quinuclidinone 
• 120-57-0 piperonal 
• 1193-65-3 3-quinuclidinone hydrochloride 

Relevant academic research and scientific papers

Ruthenium-Catalyzed Highly Enantioselective Synthesis of cis-3-Quinuclidinols via DKR Asymmetric Transfer Hydrogenation

A method for the enantioselective synthesis of cis-3-quinuclidinols by Ru-catalyzed asymmetric transfer hydrogenation via dynamic kinetic resolution is described. The reaction proceeded under mild conditions using ammonium formate as the hydrogen donor, affording the products in high yields (up to 99%) with excellent diastereoselectivity (up to 99:1 dr) and enantioselectivity (95-99% ee). This protocol was applicable to gram-scale preparation with perfect enantioselectivity through simple recrystallization.

Synthetic entry to tricyclic and tetracyclic quinuclidine derivatives by cycloaddition and ring transformation

The (Z)-2-arylidene-quinuclidines 5-8 were synthesized. Their reaction with aliphatic dibasic functional reagents in both basic and acidic conditions afforded the fused heterocycles 9, 10 and 11. However, the reaction of arylidene derivative 5 with an aromatic dibasic functional reagent gave benzimidazole 13 in lieu of the anticipated tetracyclic system, quinuclidino[3,2-e]benzo[b]-1,4- diazepine 12. Cycloadditions of 5 with different reagents gave the heterocyclic derivatives 17, 19, 22 and 23. Acid-catalyzed cyclization of 5 with excess resorcinol gave 24. Compounds 9a, 19 and 24 showed antibacterial activities.