52482-19-6

Upstream product

• 3295-64-5 1,2,3,4-tetrahydroacridine 
• 100-52-7 benzaldehyde 
• 271-58-9 anthranil 
• 636-82-8 cyclohexene-1-carboxylic acid 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 52482-13-0 3'-phenyl-2,3-dihydro-1H-spiro[acridine-4,2'-oxirane] 
• 118718-61-9 4-(1-Phenyl-propyl)-1,2,3,4-tetrahydro-acridine 
• 118718-63-1 4-(1-Phenyl-hexyl)-1,2,3,4-tetrahydro-acridine 
• 118718-45-9 4-(Naphthalen-1-yl-phenyl-methyl)-acridine 
• 118718-43-7 4-(1-Phenyl-hexyl)-acridine 
• 118718-42-6 4-(1-Phenyl-butyl)-acridine 
• 118718-44-8 4-Benzhydryl-acridine 
• 118718-41-5 4-(1-Phenyl-propyl)-acridine 
• 118718-40-4 4-(Naphthalen-1-yl-phenyl-methyl)-1,2,3,4-tetrahydro-acridine 
• 118718-64-2 4-Benzhydryl-1,2,3,4-tetrahydro-acridine 
• 118718-62-0 4-(1-Phenyl-butyl)-1,2,3,4-tetrahydro-acridine 

Relevant academic research and scientific papers

Synthesis of (E)-2-Alkenylazaarenes via Dehydrogenative Coupling of (Hetero)aryl-fused 2-Alkylcyclic Amines and Aldehydes with a Cobalt Nanocatalyst

To date, the synthesis of (E)-2-alkenylazaarenes via the condensation of 2-methyl N-heteroarenes with aldehydes or their equivalents has been well demonstrated. However, the direct formation of such a class of useful compounds from extensively distributed 2-alkylcyclic amine motifs remains an unresolved goal. Herein, by employing the nitrogen-silica-doped carbon (Vulcan XC-72R) as the support, we have developed a low-loading cobalt nanocatalyst (Co/N-Si-C). The combination of such a catalyst with p-nitrobenzoic acid and molecular O2 exhibits excellent catalytic performance towards the dehydrogenative coupling of (hetero)aryl-fused 2-alkylcyclic amines with aldehydes to afford the (E)-2-alkenylazaarenes. In the reaction, effective capture of the partially dehydrogenated cyclic amine motifs appears to be the key strategy to address the issue of the chemoselectivity. The developed catalytic transformation proceeds with the merits of broad substrate scope, good functional group tolerance, high atom-efficiency, use of an earth-abundant and reusable cobalt catalyst and molecular O2 as a green oxidant, which offers an important basis for the direct conversion of inert cyclic amine units into the functional frameworks.

Rh-Catalyzed C-H Amination/Annulation of Acrylic Acids and Anthranils by Using -COOH as a Deciduous Directing Group: An Access to Diverse Quinolines

A method for the synthesis of diverse polysubstituted quinolines from readily available acrylic acids and anthranils has been developed. The weakly coordinating -COOH directing group, which can be tracelessly removed in the cascade cyclization, is essential for this reaction. Diverse polysubstituted quinolines were obtained under mild reaction conditions with simple H2O and CO2 as byproducts. More importantly, 1,2,3,4-tetrahydroacridine, which is the core skeleton of tacrine (an Alzheimer's disease drug), was conveniently synthesized.

Direct alkenylation of alkylazaarenes with aldehydes through C(sp3)-H functionalization under catalytic InCl3 activation

Under the influence of InCl3 as a Lewis acid catalyst, a methodology on the C(sp3)-H functionalization of alkylazaarenes has been demonstrated through the activation of benzylic C-H bonds towards their addition reaction with the appropriate electrophiles. This methodology was chiefly applied in the direct alkenylation of primary and secondary benzylic C-H bonds of alkylazaarenes with aldehydes. A variety of alkenyl products were afforded in generally good yields including the starting alkenyl intermediate used in the synthesis of montelukast and other related molecules.