33670-02-9

Upstream product

• 52190-35-9 2-(methylthio)cyclohexanone 
• 62-53-3 aniline 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 2207-96-7 methyl 2-phenyldiazene-1-carboxylate 
• 108-94-1 cyclohexanone 
• 100-65-2 N-Phenylhydroxylamine 
• 586-96-9 Nitrosobenzene 
• 7429-44-9 2-methoxycyclohexanone 
• 23740-64-9 2-morpholinocyclohex-2-enone 
• 484696-92-6 2-(N-phenylaminooxy)cyclohexanone 

Downstream Products

• 129340-55-2 2,3-dimethyl-7-oxo-1-phenyl-4,5,6,7-tetrahydroindole 
• 130919-72-1 1-ethoxycarbonylamino-3-phenyl-2,3,4,5,6,7-hexahydrobenzimidazol-2,4-dione 
• 130919-66-3 2-(N-ethoxycarbonyl-N-phenyl)amino-3-(N'-ethoxy-carbonyl)-hydrazinocyclohex-2-en-1-one 
• 130919-63-0 2-phenylamino-3-(N,N'-diethoxycarbonyl)hydrazinocyclohex-2-en-1-one 
• 129340-57-4 2-methyl-7-oxo-1,3-diphenyl-4,5,6,7-tetrahydroindole 
• 129340-56-3 <4R^*-(4α,4aα,8aα)>-4,4a,5,6,7,8-hexahydro-3-methyl-8-oxo-4-phenyl-8a-phenylamino-4H-1,2-benzoxazine N-oxide 
• 129340-41-6 <3R^*-(3α,3aα,6aα)>-6a-hydroxy-2-nitro-3-phenylhexahydro-1(2H)-pentalenone 
• 129340-54-1 <1R^*-(1α,6α,7α,8β)>-8-nitro-7-phenyl-1-phenylaminobicyclo<4.2.0>octan-2-one 
• 129340-63-2 <4aR^*-(4aα,10aβ,10bα)>-1,2,3,4,4a,8,9,10,10a,10b-decahydro-4-oxo-4a-phenylamino-7H-dibenzo-1,2-oxazine N-oxide 
• 129340-61-0 <4R^*-(4α,4aα,8aα)>-4,4a,5,6,7,8-hexahydro-8-oxo-3,4-diphenyl-8a-phenylamino-4H-1,2-benzoxazine N-oxide 
• 129340-60-9 3-methyl-7-oxo-1,2-diphenyl-4,5,6,7-tetrahydroindole 
• 130920-12-6 1-benzylamino-3-phenyl-2,3,4,5,6,7-hexahydrobenimidazol-2,4-dione 
• 130919-67-4 -(N-etxoxycarbonyl-N-phenyl)amino-3-(N'-benzoyl)-hydrazinocyclohex-2-en-1-one 
• 130919-64-1 2-phenylamino-3-(N-ethoxycarbonyl-N'-benzoyl)hydrazinocyclohex-2-en-1-one 

Relevant academic research and scientific papers

Can Primary Arylamines Form Enamine? Evidence, α-Enaminone, and [3+3] Cycloaddition Reaction

The formation of enamine from primary arylamines was detected and confirmed by nuclear magnetic resonance spectroscopy. The presence of a radical quencher, e.g., (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl, was found to be essential for the detection of enamine formation. A direct synthesis of α-enaminones from primary arylamines and ketones was also developed. Mechanistic investigation of α-enaminone formation suggests that an amine radical cation generated through O2 singlet energy transfer was involved in initiating α-enaminone formation. The reactivity and utility of α-enaminones were explored with a [3+3] cycloaddition reaction of enones affording dihydropyridines in good yields (58-85%). α-Enaminones displayed a set of reactivities that is different from that of enamines. The knowledge gained in this work advances our basic understanding of organic chemistry, providing insights and new opportunities in enamine catalysis.

Multifunctionalization of Unactivated Cyclic Ketones via an Electrochemical Process: Access to Cyclic α-Enaminones

The multifunctionalization of unactivated cyclic ketones was developed via an electrochemically intermolecular α-amination under metal-free conditions. The reaction can be carried out smoothly with a broad scope of the aromatic amines substrates under mil

Acid/Base-Co-catalyzed Direct Oxidative α-Amination of Cyclic Ketones: Using Molecular Oxygen as the Oxidant

A novel acid/base-co-catalyzed direct intermolecular α-amination of various cyclic ketones has been developed for the first time. The reaction employs molecular oxygen as the sole oxidant under metal-free conditions. The reaction tolerates a wide range of various anilines, especially primary diamine derivatives, and provides a simple and efficient method for the constructions of α-amino enones and benzodiazepine derivatives in a single step. (Figure presented.).

Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation

A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2- enone with hypervalent iodine reagent PhI(OCOCF3)2 (PIFA), through a direct intramolecular oxidative C(sp2)-C(sp2) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]indol-6(5H)- one skeletons. The mechanism of the process was proposed and briefly discussed.

Metal-induced reactions of O-nitroso aldol products

Lewis acid catalysts play an important role in the transformation of α-aminooxy ketones (O-nitroso aldol products). Three different reactions of O-nitroso aldol products promoted by metal ions are described. Georg Thieme Verlag Stuttgart.

Copper-catalyzed amination of alkenes and ketones by phenylhydroxylamine

The catalytic activity of a number of copper complexes and salts toward allylic amination of alkenes using phenylhydroxylamine as the nitrogen fragment donor has been investigated. The best catalyst is CuCl2·2H2O, which produces moderate yields of allylamines with high regioselectivity resulting from double bond transposition. A mechanism similar to that for the molybdenum and the FePc systems is proposed. The first step in the catalytic cycle is the formation of nitrosobenzene from the oxidation of phenylhydroxylamine by Cu(II). The next step is an ene reaction of the alkene with PhNO to produce an allylhydroxylamine, which is then reduced to the allylamine product by Cu(I), thus regenerating Cu(II). The same system can also transfer the nitrogen fragment to the α-carbon of cyclic ketones; this is accompanied by dehydrogenation in some cases to produce α-aminated, α,β-unsaturated ketones.

REACTIVITY OF CYCLOPENTANONE ENAMINES TOWARDS NON-SYMMETRIC ELECTROPHILIC DIAZENES

The non-symmetric electrophilic diazenes 2 and 3 react with 1-aminocyclopentenes 1 giving enamine adducts exclusively, which have been isolated in some cases; on hydrolysis, the hydrazine substituents in the monoadducts from 2 is cleaved and only α,β-unsa