168648-70-2

Upstream product

• 59557-92-5 2-bromo-5-methoxyaniline 
• 958741-57-6 N-(2-formyl-5-methoxyphenyl)-4-methylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 536-90-3 m-Anisidine 
• 58750-87-1 N-tosyl-m-anisidine 
• 894810-81-2 N-p-toluenesulfonyl-2-ethenyl-5-methoxyaniline 
• 894810-80-1 N-(2-bromo-5-methoxyphenyl)-4-methylbenzenesulfonamide 
• 894810-41-4 N-allyl-N-(5-methoxy-2-vinyl-phenyl)-4-methyl-benzenesulfonamide 
• 333383-79-2 N-(3-methoxy-phenyl)-4-methyl-N-(3-oxo-propyl)-benzenesulfonamide 
• 168648-91-7 N-(2-[1,3]Dioxolan-2-yl-ethyl)-N-(3-methoxy-phenyl)-4-methyl-benzenesulfonamide 

Downstream Products

• 168648-78-0 N-tosyl-9-benzyloxy-8-hydroxy-3-methoxy-5-azapterocarpan 

Relevant academic research and scientific papers

Synthesis of 1,2-Dihydroquinolines via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis

The synthesis of 1,2-dihydroquinolines by the hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) of N-prenylated 2-aminobenzaldehydes is reported. Substrates with a variety of substitution patterns are shown. With an acid-labile protecting group on the nitrogen atom, in situ deprotection and autoxidation furnish quinoline. In comparison with related oxygen-containing substrates, the cycloaddition step of the catalytic cycle is shown to be slower, but the cycloreversion is found to be more facile.

Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles

A pure ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline lead to novel synthetic methods for heterocycles such as indoles and 3-methylene-2,3-dihydroindoles, which are useful synthons for bioactive natural products. These procedures address an important issue in diversity-oriented synthesis.

A practical route to quinolines from anilines

A practical route to quinoline from anilines through acid-mediated cyclization of 3-(N-aryl-N-sulfonylamino)propionaldehydes has been developed. Treatment of the cyclization products, dihydroquinoline intermediates with KOH in DMSO leads to substituted quinolines.

Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues

Oxygenated pterocarpans and 5-azapterocarpans are prepared utilizing Lewis acid-promoted reactions of 2-alkoxy-1,4-benzoquinones with 2H-chromenes and N-tosyl-1,2-dihydroquinolines, respectively. Similarly, benzannulated analogues are prepared via reactions of 5-aIkoxy-1,4-naphthoquinones with chromenes, and related 2-aryl-2,3-dihydrobenzofurans result from reactions of styrenes with the quinones. Syntheses of 5-thiapterocarpans are also described utilizing Pd(0)-coupling of o-chloromercuriophenols with 2H-chromenes.

Cycloaddition reactions of 1,4-benzoquinone mono- And bisimides with styrenyl systems: New syntheses of nitrogen substituted azapterocarpans, pterocarpans, 2-aryl-2,3-dihydroindoles and -dihydrobenzofurans

Lewis acid-promoted reactions of 1,4-benzoquinones and 1,4-benzoquinone bis- and monoimides with various 2H-chromenes, N-tosyl-1,2-dihydroquinolines and styrenes regio- and stereoselectively produce the title compounds in good yields.