20150-89-4

Upstream product

• 108-69-0 3,5-dimethylaminoaniline 
• 156-87-6 propan-1-ol-3-amine 
• 3179-63-3 3-Dimethylamino-1-propanol 
• 99-12-7 5-nitro-m-xylene 
• 14002-34-7 tripropanolamine 
• 77611-71-3 1,2-bis(3,5-dimethylphenyl)diazene 
• 106-95-6 allyl bromide 
• 504-63-2 trimethyleneglycol 
• 107-18-6 allyl alcohol 
• 56-81-5 glycerol 

Downstream Products

• 57414-68-3 5,7-dimethyl-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Ruthenium-Catalyzed Formation of Quinolines via Reductive Cyclization of Nitroarenes with Tris(3-hydroxypropyl)amine in an Aqueous Medium

Nitroarenes react with tris(3-hydroxypropyl)amine in an aqueous medium (dioxane/H2O) at 180° in the presence of a catalytic amount of a ruthenium catalyst and tin(II) chloride along with isopropanol as hydrogen donor to afford the corresponding quinolines in good yields. The presence of tin(II) chloride is essential for the formation of quinolines. A reaction pathway involving initial reduction of nitroarenes to anilines, propanol group transfer from tris(3-hydroxypropyl)amine to anilines to form 3-anilino-l-propanols, N-alkylation of anilines by 3-anilino-1-propanol to form 1,3-dianilinopropane and intramolecular heteroannulation of 1, 3-dianilinopropane is proposed for this catalytic process.

Ruthenium-catalyzed synthesis of quinolines via reductive heteroannulation of nitroarenes with 3-amino-1-propanols

Nitroarenes are reductively cyclized with 3-amino-1-propanols in dioxane/H2O in the presence of a ruthenium catalyst and tin(II) chloride dihydrate together with isopropanol to afford the corresponding quinolines. A reaction pathway involving i

Synthesis of quinolines by ruthenium-catalyzed heteroannulation of anilines with 3-amino-1-propanol

Anilines react with 3-amino-1-propanol in dioxane in the presence of a catalytic amount of a ruthenium catalyst and tin(II) chloride dihydrate together with a hydrogen acceptor to afford the corresponding quinolines in moderate yields.

Acceptorless dehydrogenative condensation: synthesis of indoles and quinolines from diols and anilines

The use of diols and anilines as reagents for the preparation of indoles represents a challenge in organic synthesis. By means of acceptorless dehydrogenative condensation, heterocycles, such as indoles, can be obtained. Herein we present an experimental and theoretical study for this purpose employing heterogeneous catalysts Pt/Al2O3and ZnO in combination with an acid catalyst (p-TSA) and NMP as solvent. Under our optimized conditions, the diol excess has been reduced down to 2 equivalents. This represents a major advance, and allows the use of other diols. 2,3-Butanediol or 1,2-cyclohexanediol has been employed affording 2,3-dimethyl indoles and tetrahydrocarbazoles. In addition, 1,3-propanediol has been employed to prepare quinolines or natural and synthetic julolidines.

From Anilines to Quinolines: Iodide- and Silver-Mediated Aerobic Double C?H Oxidative Annulation–Aromatization

Quinoline synthesis from easily accessible raw materials such as anilines is a valuable and meaningful task. Herein, we communicate an iodide- and silver-mediated C?H/C?H oxidative annulation–aromatization between anilines and allyl alcohols. This protocol provides a direct route to the synthesis of quinoline derivatives from inexpensive commodities. Various kinds of anilines, even heterocyclic anilines, were shown to be workable substrates, generating the corresponding multi-substituted quinolines in good yields.

Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols

The cationic ruthenium-hydride complex catalyzes the dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byproducts.

Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines

A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.

Reduction of nitroarenes followed by propanol group transfer from tris(3-hydroxypropyl)- amine and cyclization leading to quinolines under heterogeneous Pd-C catalysis

Nitroarenes having electron-donating or -withdrawing substituents are reduced to anilines and cyclized with tris(3- hydroxypropyl)amine in the presence of a catalytic amount of Pd-C along with tin(II) chloride and isopropanol in dioxane-H2O medium to give the corresponding quinolines in good to excellent yields. Copyright