112403-98-2

Upstream product

• 67-62-9 O-Methylhydroxylamin 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 593-56-6 N-methoxylamine hydrochloride 
• 112404-05-4 potassium (p-methoxyphenyl)acetohydroxamate 
• 74-88-4 methyl iodide 
• 104-01-8 4-Methoxyphenylacetic acid 

Downstream Products

• 128917-49-7 2-(4-hydroxyphenyl)-N-methoxyacetamide 
• 137042-70-7 C₁₀H₁₂BrNO₂ 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 
• 104-47-2 p-methoxybenzylnitrile 

Relevant academic research and scientific papers

Photoinduced Aerobic Iodoarene-Catalyzed Spirocyclization of N-Oxy-amides to N-Fused Spirolactams**

Iodoarene catalysis is a powerful methodology that usually requires an excess of oxidant, or of redox mediator if the terminal oxidant is dioxygen, to generate the key hypervalent iodine intermediate to proceed efficiently. We report that, using the spiro-cyclization of amides as a benchmark reaction, aerobic iodoarene catalysis can be enabled by relying on a pyrylium photocatalyst under blue light irradiation. This unprecedented dual organocatalytic system allows the use of low catalytic loading of both catalysts under very mild operating conditions.

N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesizecis-enamides through vinyl benziodoxolones

The stereoselective synthesis ofcis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) fromO-alkyl hydroxamic acids in the presence of an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature. The reaction tolerated variousO-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products. Vinyl dideuteratedcis-β-N-MeO-amide-VBXs were also synthesized using deuterium oxide as the deuterium source. Valine-derivedcis-β-N-MeO-amide-VBX was stereospecifically derivatized to hydroxamic acid-derivedcis-enamides without the loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.

Spirolactams and their synthesis

New spirolactams having a benzodienone moiety and a azetidinone moiety which are highly stable due to pi interactions. They are useful as UV absorbers and as synthetic intermediates.

New spirolactams and their synthesis

New spirolactams of formula (I) having a benzodienone moiety and a azetidinone moiety which are highly stable due to pi interactions. They are useful as UV absorbers and as synthetic intermediates.

A new synthesis of nitriles from N-alkoxyimidoyl halides with zinc

Both aliphatic and aromatic nitriles are obtained from the corresponding N-methoxy-, N-benzyloxy- or N-tert-butoxyimidoyl halides with zinc in a acetic acid/dimethylformamide mixture (1:1).

Electrophilic Aromatic Substitution with N-Methoxy-N-acylnitrenium Ions Generated from N-Chloro-N-methoxyamides: Syntheses of Nitrogen Heterocyclic Compounds Bearing a N-Methoxyamide Group

N-Methoxy-N-acylnitrenium ions (II), generated by treatment of N-chloro-N-methoxyamides with silver carbonate in trifluoroacetic acid, react with arenes to give N-aryl-N-methoxyamides in good yields.In the case of the intramolecular cyclization of N-chloro-N-methoxy-2-phenylacetamides, the mode of cyclization is highly dependent on the nature of ortho or para substituent groups.Nitrenium ions II can primarily attack three positions (C-1, C-2, and C-6) of a phenyl ring.Normally II attack C-6.On the other hand, when the ortho position was occupied with a substituent group, II attacked both C-2 and C-6, in the former case followed by a 1,2-substituent migration, which was proved by a deuterium labeling experiment.Especially, when a methoxy group is substituted on ortho or para position, II attack C-1 due to the effect of the electron-releasing methoxy group to give spiro dienone compounds 39.A general discussion of the utility and mechanistic details of these reactions is presented.

N-ALKOXY-N-ACYLNITRENIUM IONS IN INTRAMOLECULAR AROMATIC ADDITION REACTIONS

N-alkoxy-N-acylnitrenium ions are generated by treatment of N-alkoxy-N-chloroamides with silver ions in ethereal solvents.These intermediates readily cyclise onto aromatic nuclei on alkoxy side-chains to give benzoxazines and benzoxazepines and on the acyl side-chains to give γ, δ and ε benzolactams.Spirane products are formed by ipso addition when a 4-methoxy substituent is present on the side-chain aromatic rings.The yields and regioselectivities of these reactions have been ascribed to different transition structures for cyclisation onto the acyl and alkoxy side-chains which involve respectively an exocyclic and endocyclic N-O ?-bond.Evidence for this exeptionally high ?-bond character has been obtained from MNDO calculations which predict a ?-bond order of 0.9 and a rotational barrier of 29.7 kcalmol-1