6829-08-9

Upstream product

• 636-82-8 cyclohexene-1-carboxylic acid 
• 4127-53-1 3-methylbenzo[c]isoxazole 
• 120-92-3 cyclopentanone 

Downstream Products

• 805227-63-8 N₃C₂₇H₁₆(CH₃)2C₆H₄N(C₄H₉)2 

Relevant academic research and scientific papers

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.

Catalyzed hydrogenation of condensed three-ring arenes and their N-heteroaromatic analogues by a bis(dihydrogen) ruthenium complex

A series of anthracene and acridine derivatives were hydrogenated under mild reaction conditions (80 °C, 3 bar of H2) using the bis(dihydrogen) complex [RuH2(η2-H2) 2{P(C6H11)3}2] (1) as a catalyst precursor. The influence of a methyl substituent on the substrate was studied. In all our systems, hydrogenation was only observed at the external rings leading to the corresponding 4H- or 8H-derivatives of anthracene and acridine. Three complexes resulting from the η4(C,C)-coordination of the substrate to the unsaturated fragment [RuH2{P(C 6H11)3}2] were characterized. In the case of 9-methyl acridine, the corresponding complex [RuH2(η 4-C14H11N){P(C6H11) 3}2] (4) turned out to be an active catalyst precursor leading to 1,2,3,4,5,6,7,8-octahydro-9-methylacridine as the sole product after 24 h. Regeneration of 1 from 4 supports the role of complex 4 in the catalytic cycle. Three hydrogenated products, 1,2,3,4-tetrahydroanthracene (4H-Anth), 1,2,3,4-tetrahydro-9-methylanthracene (4H-9-Me-Anth) and 1,2,3,4- tetrahydroacridine (4H-Acr), were characterized by X-ray diffraction. The Royal Society of Chemistry 2012.

Unprecedented hydrothermal reaction of o-phenylaniline and related derivatives with cyclic ketones. A novel approach to the construction of phenanthridine and quinoline ring systems

(Matrix presented) A new method for synthesizing phenanthridine and its related compounds was developed using the condensation of o-phenylaniline and its homologues with cyclic ketones under hydrothermal conditions.