58153-99-4

Upstream product

• 94-38-2 3-diethylamino-1-phenyl-propan-1-one 
• 20265-96-7 p-chloroaniline hydrochloride 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 
• 106-47-8 4-chloro-aniline 
• 50-00-0 formaldehyd 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 7661-27-0 N-(4'-chlorophenyl)-2-azetidinone 
• 71-43-2 benzene 
• 5409-66-5 3-benzoyl-4-hydroxy-1-methyl-4-phenylpiperidine 
• 2298-49-9 N-methyl-3-oxo-N-(3-oxo-3-phenylpropyl)-3-phenylpropan-1-aminium chloride 
• 3506-36-3 3-dimethylaminopropiophenone 
• 768-03-6 Phenyl vinyl ketone 
• 93-55-0 1-phenyl-propan-1-one 
• 936-59-4 3-chloropropiophenone 

Downstream Products

• 15145-57-0 1-Phenyl-3-(p-chlor-anilino)-propanol-⁽¹⁾ 
• 89410-03-7 2-Chloro-3-(4-chloro-phenyl)-6-phenyl-[1,3,2]oxazaphosphinane 2-oxide 
• 89410-09-3 2-Aziridin-1-yl-3-(4-chloro-phenyl)-6-phenyl-[1,3,2]oxazaphosphinane 2-oxide 
• 1048974-43-1 1-(3,4,5-trimethoxyphenyl)-3-(4-chlorophenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-one 
• 1048974-40-8 1,3-bis(4-chlorophenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-one 
• 1048974-41-9 1-(4-methylphenyl)-3-(4-chlorophenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-one 
• 1048974-42-0 1-(4-methoxyphenyl)-3-(4-chlorophenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-one 
• 1325232-95-8 3,4,5,6-tetrahydro-4-(p-chlorophenyl)-2-(p-nitrophenyl)-7-phenyl-2H-1,2,4-triazepine 

Relevant academic research and scientific papers

Synthesis of 3-aroyl-4-hydroxy-4-arylpiperidine derivatives by DBU-catalyzed reactions of amines with vinyl ketones

In one-pot cascade reaction, a series of functionalized 3-aroyl-4-hydroxy-4-arylpiperidine derivatives were prepared from sulfonamides and vinyl ketones with good to excellent yields and diastereoselectivities. The reaction was catalyzed by the commercially available Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and could be easily manipulated under mild condition. Georg Thieme Verlag Stuttgart · New York.

I2-Promoted Intramolecular Oxidative Cyclization of Butenyl Anilines: A Facile Route to Benzo[b]azepines

A metal-free approach for the synthesis of seven-membered N-heterocycles has been developed by the I2-promoted intramolecular cross-coupling/annulation of butenyl anilines. This cyclization reaction involves C?H activation and C?C bond formation and exhibits good functional group tolerance. A series of benzo[b]azepine derivatives are obtained in moderate to good yields.

Iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to form β-aminoketones and Benzo[h]quinolones

An iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to yield β-aminoketones and benzo[h]quinolones had been developed. Noble metallic catalysts, oxidants, α β-unsaturated ketone intermediates and aza-Michael addition were not involved in this coupling reaction which made it unique when compared to other reactions reported in literature. Inexpensive iodine catalyst, easy accessible raw materials, mild reaction conditions, good functional group tolerance and excellent selectivity made this coupling reaction be a practical method. This reaction can also be scaled up.

Cu-catalyzed sequential dehydrogenation-conjugate addition for β-functionalization of saturated ketones: Scope and mechanism

The first copper-catalyzed direct β-functionalization of saturated ketones is reported. This protocol enables diverse ketones to couple with a wide range of nitrogen, oxygen and carbon nucleophiles in generally good yields under operationally simple conditions. The detailed mechanistic studies including kinetic studies, KIE measurements, identification of reaction intermediates, EPR and UV-visible experiments were conducted, which reveal that this reaction proceeds via a novel radical-based dehydrogenation to enone and subsequent conjugate addition sequence.

Aza-Michael reaction promoted by aqueous sodium carbonate solution

A general and efficient aza-Michael reaction promoted by aqueous sodium carbonate solution has been developed. The reaction has complete mono-alkylation selectivity and proceeds with complete chirality retention for chiral amino esters. With a broad substrate scope, a well-common catalyst and simple operation, the catalytic approach provides a facile, practicable, economical, and environmentally benign method for the synthesis of β-amino carbonyl compounds.

Mannich bases as synthetic intermediates: Convenient synthesis of functionalized 1,2,4-triazepines, 1,4-diazepines and 1,5-diazocines

Transamination between the ketonic Mannich bases 1a, b and primary arylamines gave a series of ketonic sec-Mannich bases 2a - h. A variety of tetrahydro-1,2,4-triazepines 3a - f have been synthesized by treating the arylhydrazones of 2 with formaldehyde. A similar reaction with the benzenesulfonylhydrazone of 2b afforded 4. The 3-styryl-2H-1,2,4-triazepine 5 was obtained from the phenylhydrazone of 2a and cinnamaldehyde. Treatment of arylhydrazones of the 4-methoxystyryl keto base 7 with formaldehyde and cinnamaldehyde afforded the 3,4,5,6-tetrahydro-2H-1,2,4-triazepines 8a, b. Mannich reaction with 4-(p-hydroxyphenyl)-tetrahydro-1,2,4-triazepine 3d afforded the Mannich bases 9, 10 and 11. The reaction of 1b with o-phenylenediamine leads to the 1,5-benzodiazepine 13. The new tetrahydro- 1,4-diazepine and tetrahydro-1,5-diazocine Mannich bases 15 and 17 were obtained from 1b and ethylenediamine or 1,3-diaminopropane, respectively. The bi(piperidine) derivative 19 was obtained from 1a and 1,3-diaminopropane.

Amine exchange reactions in ionic liquid

An operationally simple, inexpensive, efficient, and environmentally friendly protocol for the amine exchange reactions of 3-N,N- dimethylaminopropiophenone and N,N-dimethylaminomethylferrocene with primary aryl amines is developed using the ionic liquid

Mannich bases as synthetic intermediates: Alkylation of amines and diamines with bis-ketonic Mannich bases

The bis-ketonic Mannich base, N,N-bis(β-benzoylethyl)methylamine hydrochloride (1) reacts with primary arylamines and diamines to give ketonic sec-arylamines 3a-e and 4. The piperidines 7a-c were obtained from 1 and primary alkylamines, whereas the 1,4-diazepine derivative 10 was obtained from 1 and ethylenediamine. Treatment of the bis-base l,4-di[β-(N-morpholino) propionyl]benzene bis(hydrochloride) (11) with primary arylamines gave the corresponding bis-(sec-arylamines) 12a - b, whereas its reaction with o-phenylenediamine afforded the bis[1,5-benzodiazepine] ring system 14. The synthesis of the diazacyclophane ring system 15 has been achieved by treating 11 with piperazine. Attempted synthesis of 4-aza-[7]-paracyclophane (16) from 11 and benzylamine led to 17. The reaction of 1 or 11 with phenylhydrazine gave the 2-pyrazolines 18 and 19. Treatment of 3 or 4 with phenylhydrazine and formaldehyde afforded the 2H-1,2,4-triazepines 20a-c and the bis[2H-1,2,4-triazepine] ring system 21.

A convenient synthesis of novel 1,3,4-triaryl-3,4-dihydropyrimidin-2(1H)- ones by cyclization of aromatic isocyanates with β-arylamino-1- phenylpropan-1-ones

(Chemical Equation Presented) A simple one-step method for preparation of novel 1,3,4-triaryl-3,4-dihydropyrimidin-2(1H)-ones has been developed by reaction of aromatic isocyanates with β-arylamino-1-phenylpropan-1-ones in refluxing toluene in the presence of KHSO4 and HCl.

Conversion of 3-benzoyl-1-methyl-4-phenyl-γ-piperidol by arylamines and arylhydrazines. Synthesis of 3-arylamino-1-oxo-1-phenylpropanes and 1,3-diarylpyrazoles and their fragmentation under electron impact

It has been established that on heating, 3-benzoyl-4-hydroxy-1-methyl-4- phenylpiperidine is ring-opened in the presence of arylamines by a type of retroaldol reaction, with subsequent transamination of the intermediate Mannich base and the formation of 3-arylamino-1-oxo-1-phenylpropanes. When using arylhydrazines this γ-piperidol is recyclized with the formation of 1,3-diarylpyrazoles and their 4,5-dihydro derivatives. The mass spectral behavior of a series of 3-arylamino-substituted 1-phenylpropanones has been studied.