91523-28-3

Upstream product

• 112403-78-8 N-phenylacetyl-O-methylhydroxylamine 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 112404-03-2 potassium phenylacetohydroxamate 

Downstream Products

• 65816-14-0 1-methoxyindolin-2-one 
• 121990-00-9 N-methoxy-N-phenyl-2-phenylacetamide 
• 165754-55-2 HUN-7293 

Relevant academic research and scientific papers

Total synthesis of HUN-7293

The first total synthesis of the cyclic heptadepsipeptide HUN-7293 (1), a potent inhibitor of cell adhesion molecule expression exhibiting anti-inflammatory properties, is detailed. The most effective approach relied on an unusually efficient macrocyclization with the formation of the MLEU3 - LEU4 secondary amide that potentially benefits from intramolecular H-bonding preorganization of the acyclic substrate. The requisite linear depsipeptide was convergently assembled with the late stage introduction of the linking ester enlisting a Mitsunobu esterification that occurs with inversion of the DGCN α-center permitting the utilization of a readily available L-amino acid precursor to the D α-hydroxy carboxylic acid residue. An alternative and similarly attractive approach of direct macrolactonization of a substrate necessarily incorporating a D-DGCN subunit proved viable albeit less effective. Biological evaluation in cellular assays for vascular adhesion molecule expression confirmed that synthetic HUN-7923 (1) is essentially indistinguishable from the naturally occurring cyclodepsipeptide.

Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: Structures, syntheses and antifungal activity

Phytoalexins are inducible chemical defenses produced by plants in response to diverse forms of stress, including microbial attack. Our search for phytoalexins from cruciferous plants resistant to economically important fungal diseases led us to examine s

New 3-(hydroxybenzylidenyl)-indolin-2-ones

The invention relates to a compound selected from those of formula (I): STR1 wherein R1, R2, R3, R4, R5 and X are as defined in the description, its Z and E isomers, its optical isomers, in pure form

CYCLIZATION WITH NITRENIUM IONS GENERATED FROM N-METHOXY- OR N-ALLYLOXY-N-CHLOROAMIDES WITH ANHYDROUS ZINC ACETATE. SYNTHESIS OF N-HYDROXY- AND N-METHOXYNITROGEN HETEROCYCLIC COMPOUNDS

Electrophilic intramolecular aromatic substitution with an N-methoxy- or an N-allyloxyacylnitrenium ion, generated by treatment of an N-methoxy- or an N-allyloxy-N-chloroamide with anhydrous zinc acetate in nitromethane, leads to formation of a nitrogen h

A new synthesis of N-alkoxy-2-ethoxyarylacetamides from N-alkoxy-N-chloroarylacetamides with triethylamine in ethanol

Treatment of N-alkoxy-N-chloroarylacetamides with triethylamine in ethanol results in removal of a chlorine atom and introduction of an ethoxy group at the C-2 position of arylacetamides in moderate yields.

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

Intramolecular Cyclization with Nitrenium Ions Generated from N-Chloro-N-methoxyamides in Neutral Conditions

Intramolecular aromatic substitution by a N-chloro-N-methoxyamide group to a suitably situated aromatic ring in the molecule is performed by using anhydrous zinc acetate and nitromethane as solvent to give nitrogen heterocycles in good yield.