1557-41-1

Upstream product

• 372109-36-9 1-(2-benzyl-phenyl)-6-hydroxy-piperidin-2-one 
• 64-18-6 formic acid 
• 28059-64-5 2-benzylaniline 
• 372109-30-3 1-(2-benzyl-phenyl)-piperidine-2,6-dione 

Downstream Products

• 256-86-0 Morphanthridine 
• 146446-96-0 1-benzyl-2-isocyanatobenzene 
• 1582273-47-9 phenethyl (2-benzylphenyl)carbamate 
• 449-55-8 6,11-dihydro-5H-dibenzo[b,e]azepine 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship of 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives: A novel series of 5-HT2A/2C receptor antagonists. Part 1

The synthesis of a series of novel 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives as well as their 5-HT2A/2C and H1 receptor binding affinities are described. The in vivo activity as potential anxiolytics of the synthesised compounds was measured in a mCPP challenge test. One of the compounds, 2a, proved to be a potent 5-HT2A/2C receptor antagonist showing as well oral activity and therefore could be considered as a potential anxiolytic/antidepressant agent.

Palladium-catalyzed secondary benzylic imidoylative reactions

Reported herein is a palladium-catalyzed secondary benzylic imidoylative Negishi reaction leveraging the sterically bulky aromatic isocyanides as the imine source. This method allows the facile access of alkyl-, (hetero)aryl-, and alkynylzinc reagents to afford various α-substituted phenylacetone products under mild acidic hydrolysis, which are ubiquitous motifs in many pharmaceuticals and biologically active compounds. The diastereoselective reduction of imine can be accomplished to provide the expedient conversion of secondary benzylic halide into α-substituted phenethylamine derivatives with high atom economy.

Synthesis of tetracyclic DIBENZO[c,f]azepine and benzo[f]thieno[3,2-c]azepine derivatives via N-acyluminium ion cyclization

Tetracyclic dibenzo[c,f]-4-oxopyrrolo[1,2-c]azepine (2a), dibenzo[c,f]-5-oxopiperido[1,2-c]azepine (2b), benzo[f]-4-oxopyrrolo[1,2-a]thieno[3,2-c]azepine (2c), and benzo[f]-5-oxopiperido[1,2-a]thieno[3,2-c]azepine (2d) were prepared through intramolecular N-acyliminium ion cyclization of hydroxylactams (3a-d) with aromatic or heteroaromatic rings such as benzene and thiophene as a π-nucleophile. In the case of furan ring, the hydroxylactams (3e, f) were completely decomposed under the acidic conditions (formic acid or methanesulfonic acid). Subsequent reduction of 2a-d with BF3·O(C2H5)2 and BH3·S(CH3)2 finally provided the tetracyclic dibenzo[c,f]pyrrolo[1,2-c]azepine (1a), dibenzo[c,f]piperido[1,2-c]azepine (1b), benzo[f]pyrrolo[1,2-a]thieno[3,2-c]azepine (1c), and benzo[f]piperido[1,2-a]thieno[3,2-c]azepine derivatives (1d) as analogues of mianserin.