69906-07-6

Usage

Physical state

Yellow to amber colored liquid

Odor

Strong and pungent

Uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals, production of dyes, perfumes, and other organic compounds

Reactivity

Versatile

Role

Building block for the creation of new chemical compounds

Importance

Potential as a key precursor in the synthesis of important molecules, of interest to researchers and chemists in the field of organic chemistry.

Upstream product

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 766-05-2 cyclohexane carbonitrile 
• 931-53-3 Cyclohexyl isocyanide 
• 38707-70-9 8-formylquinoline 

Downstream Products

• 1262448-76-9 (E)-N-((1,2,3,4-tetrahydroquinolin-8-yl)methylene)-2-methylcyclohexan-1-amine 

Relevant academic research and scientific papers

1,5-Hydride-Shift-Triggered Cyclization for the Synthesis of Unsymmetric Julolidines

Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride-shift-triggered cyclization to provide difficult to access julolidine derivatives in yields of 21 98% under scandium(III) triflate catalysis. Additionally, the scope of the reaction, several follow-up transformations and a remarkable side process discovered during optimization of the conditions are highlighted.

A Modular Approach to Dibenzo-fused ?-Lactams: Palladium-Catalyzed Bridging-C?H Activation

Tricyclic ring systems possessing a dibenzo structure joined to a seven-membered heterocyclic ring frequently show important biological activities. However, a modular approach to these molecules based on efficient intermolecular reaction of readily available chemicals is lacking. Herein, an unprecedented palladium-catalyzed formal [4+3] annulation for modular construction of these tricyclic systems is described. This reaction features easily accessible reactants (o-haloarylaldehydes and N-tosylhydrazones), broad substrate scope, and excellent functional group compatibility. The synthetic potential is demonstrated by the easy scale-up reactions, late-stage modification of complex molecules, and collective synthesis of bioactive molecules and approved drugs.

Chemoselective reduction of heteroarenes with a reduced graphene oxide supported rhodium nanoparticle catalyst

Rhodium nanoparticles immobilized on reduced graphene oxide were obtained from the microwave-induced thermal decomposition of Rh6(CO)16 in the ionic liquid [bmim][BF4] (bmim = 1-butyl-3-methylimidazolium cation) in the absence of additional stabilizing agents. The resulting rhodium nanoparticles are 99%, without interfering with other reducible groups, and with high conversions. Related catalysts prepared using conventional thermal heating were prepared for comparison purposes and were found to be considerably less active.

A Rhodium Nanoparticle-Lewis Acidic Ionic Liquid Catalyst for the Chemoselective Reduction of Heteroarenes

We describe a catalytic system composed of rhodium nanoparticles immobilized in a Lewis acidic ionic liquid. The combined system catalyzes the hydrogenation of quinolines, pyridines, benzofurans, and furan to access the corresponding heterocycles, important molecules present in fine chemicals, agrochemicals, and pharmaceuticals. The catalyst is highly selective, acting only on the heteroaromatic ring, and not interfering with other reducible functional groups.

Investigations concerning the organolanthanide and group 3 metallocene-catalyzed cyclization-functionalization of nitrogen-containing dienes

Organolanthanide catalyzed cyclization-silylation of nitrogen-containing polyunsaturated systems allows access to core structures commonly found in naturally occurring alkaloids. Nitrogen-containing dienes with various substitution patterns were investigated. The method was most successful for substrates with terminal alkenes. Cyclization upon pendant 1,1-disubstituted olefins was not realized under various conditions. Interestingly, sterically hindered sulfonamides, which were previously believed to render the catalyst inactive, were actually compatible with the catalyst, thus affording the cyclized products after prolonged reaction times. Variations using fused ring systems were also investigated.