56570-44-6

Upstream product

• 74-89-5 methylamine 
• 3306-07-8 1-benzoyl-2-chloroethene 
• 137661-28-0 N-methyl-N-(3,5-diphenyl-4-isoxazolylmethyl)amine 
• 41125-10-4 benzoylacetaldehyde sodium salt 
• 593-51-1 methylamine hydrochloride 
• 1131-80-2 (E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 98-86-2 acetophenone 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 53995-89-4 5-benzoyl-1-methylpyridin-2(1H)-one 
• 115290-81-8 (R)-N-methyl-3-phenyl-3-hydroxypropylamine 
• 114133-37-8 (S)-N-methyl-3-amino-1-phenyl-1-propanol 
• 1351468-93-3 (R)-N-(3-hydroxy-3-phenylpropyl)-N-methylacetamide 

Relevant academic research and scientific papers

An efficient method for the synthesis of 2-pyridones: Via C-H bond functionalization

A simple and practical method to access N-substituted 2-pyridones via a formal [3+3] annulation of enaminones with acrylates based on RhIII-catalyzed C-H functionalization was developed. Control and deuterated experiments led to a plausible mechanism involving C-H bond cross-coupling and aminolysis cyclization. This strategy provides a short synthesis of structural motifs of N-substituted 2-pyridones.

Ruthenium-catalyzed asymmetric hydrogenation of β-keto- enamines: An efficient approach to chiral γ-amino alcohols

A highly efficient and enantioselective hydrogenation of unprotected β-ketoenamines catalyzed with ruthenium(II) dichloro{(S)-(-)-2,2′- bis[di(3,5-xylyl)phosphino]-1,1′-binaphthyl}[(2S)-(+)-1, 1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine] {Ru[(S)-xylbinap][(S)-daipen] Cl2} has been successfully developed. This methodology provides a straightforward access to free γ-secondary amino alcohols, which are key building blocks for a variety of pharmaceuticals and natural products, with high yields (>99%) and excellent enantioselectivities (up to 99% ee) in all cases. Copyright

KHSO4 assisted Michael addition-elimination reactions of formylated acetophenones in water: A facile general green synthetic route to 3-(alkyl/aralkyl/aryl)amino-1-arylprop-2-en-1-ones

A facile general green synthetic route to 3-(alkyl/aralkyl/aryl)amino-1- arylprop-2-en-1-ones in excellent yields has been developed by reacting formylated acetophenones with primary amines assisted by KHSO4 in water.

A facile route to enaminones: Synthesis of 3-alkyl/aralkyl/arylamino-1- arylprop-2-en-1-ones

Reactions of 3-dimethylamino-1-arylprop-2-en-1-ones 2 with arylamines in acetic acid at room temperature and with alkylamines or aralkylamines in refluxing ethanol give 3-arylamino-1-arylprop-2-en-1-ones 3a-j and 3-alkyl/aralkylamino-1-arylprop-2-en-1-one

Reaction of enaminones with thiacumulenes

Enaminones 2, easily prepared from the corresponding sodium salts of ss-ketoaldehydes 1 and hydrochlorides of primary amines, react with carbon disulfide/ sodium hydride to give dithiocarbamates 3 after alkylation. In a similar way thiocarbamoylation yields isothioureas 4. The 13C NMR parameters of 2, 3 and 4 show significant low- and high-field shifts of the C-1 and C-2 signals, respectively.

Deuterium isotope effects on 13C chemical shifts of enaminones

Deuterium isotope effects on 13C chemical shifts have been studied in a series of substituted N-alkyl and N-phenyl keto-enamines. The intramolecularly hydrogen bonded Z-forms show the largest two-bond isotope effects, 2δC-1 (ND). Methyl-substitution at C-1 leads to a larger two-bond isotope effect in the N-phenyl-substituted derivatives. This effect is ascribed to steric compression. Space-filling substituents at the ortho-position of the N-phenyl ring lead to a decrease of the two-bond isotope effect. A correlation is found between 2δC-1(ND) and 3δC-2′(ND). The latter becomes negative in the sterically hindered cases. 3δC-2′(ND) may therefore be used as a gauge of the twist of the phenyl ring. o-Hydroxy substitution of the CO-phenyl rings enables intramolecular hydrogen bonding to the carbonyl group. This kind of hydrogen bond with two donors to one acceptor leads to smaller 2δC-2(ND) and 2δC-2″(OD) isotope effects equivalent to weaker hydrogen bonds for the Z-isomer. This is ascribed to competition for the acceptor. For the E-isomer 2δC(OD) is enhanced. The same feature is seen for N,N-dimethylamino enamines. This increase is ascribed to delocalization of the nitrogen lone-pair onto the carbonyl oxygen, thereby strengthening the hydrogen bond and thus leading to larger two-bond, 2δC(OD), isotope effects. Acta Chemica Scandinavica 1997.

Photoreactivity of 4-nucleophile-substituted isoxazoles

The photoreactivity of 1a-1c under steady-state irradiation has been examined and the photoproducts characterized.Several heterocycloes were obtained: 1a gave the pyrrazolines 6 and 7 and the triazine 8; 1b yielded the azetidine 9 and the imidazole 10; 1c gave the imidazole 10, the piperazine 15, the aziridine 16 and the pyrazole 19.In addition, open-chain products were obtained, i.e., the methylaminovinyl ketone 12 from 1b and the enaminones 17 and 18 from 1c.While the formation of most of the products can be explained via the expected intermediate ketenimines, azirines and nitrile ylides, new pathways are involved in the formation of the isoxazole 13 and the pyrazole 19 from 1c