176103-90-5

Usage

Type of compound

Heterocyclic compound
Contains a benzotriazole ring and a quinoline ring.

Importance in medicinal chemistry

Both benzotriazole and quinoline rings are significant structural motifs.

Potential applications

Pharmaceutical industry (building block for synthesis of biologically active molecules)
Drug discovery and development (due to its unique structure and properties)
Other fields (e.g., materials science and chemical synthesis)

Need for further research

To fully understand its capabilities and potential applications.

Upstream product

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 28539-02-8 1-Hydroxymethyl-1H-benzotriazole 

Relevant academic research and scientific papers

Convenient synthesis of julolidines using benzotriazole methodology

Reaction of N,N-bis[(benzotriazol-1-yl)methyl]aniline (2) with 1-vinylpyrrolidin-2-one gives a mixture of diastereomeric 1,7-bis(2-oxopyrrolidin-1-yl)julolidines 3. After reduction of 3 with LAH, the predominant trans diastereomer of 1,7-di(pyrrolidin-1-yl)julolidine (4) is separated. Reaction of 2 with ethyl vinyl ether yields predominantly trans-1,7-di(benzotriazol-1-yl)julolidine (11). Stepwise synthesis from tetrahydroquinoline 15 gives access to julolidines with two different substituents on C-1 and C-7. Reaction of 1-[(benzotriazol-1-yl)methyl]-1,2,3,4-tetrahydroquinoline (25) with enolizable aldehydes gives a mixture of tetrahydroquinolines 26-29 which are converted into single julolidine products upon treatment with sodium hydride, LAH, or phenylmagnesium bromide. Reactions of 1,2,3,4-tetrahydroquinolines with benzotriazole and 2 molar equiv of enolizable aldehydes gives 1,2,3-trisubstituted julolidines 38-41, which with lithium aluminum hydride, sodium hydride, or a Grignard reagent produce single diastereomers of products 42, 43, and 45, respectively.