64682-89-9

Upstream product

• 501-53-1 benzyl chloroformate 
• 95-55-6 2-amino-phenol 
• 88-75-5 2-hydroxynitrobenzene 
• 5366-26-7 <2-Nitro-phenyl>--ether 

Downstream Products

• 110877-44-6 [2-(2-piperidino-ethoxy)-phenyl]-carbamic acid benzyl ester 
• 1407484-74-5 benzyl 2H-benzo[b][1,4]oxazine-4(3H)-carboxylate 
• 376592-93-7 3′-amino-2′-hydroxy biphenyl-3-carboxylic acid 

Relevant academic research and scientific papers

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp2)-H or C(sp3)-H: Nitration via C-N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water

A novel nitration (via C(sp3)-N breaking/C(sp2)-N formation with CH3NO2) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO2 transfer from CH3NO2 to the aromatic group of the substrate is possible with careful selection of the solvent, NaX, and oxidant. In addition, the solvent-controlled C(sp2)-H functionalization can shift to an α-C(sp3)-H functionalization (cyanation or oxygenation) of the α-C(sp3)-H of cyclic amines.

A New Deprotection Procedure of MTM Ether

A new deprotection procedure of methylthiomethyl (MTM) ether, a protective group for the hydroxy group, was developed. MTM was oxidized with MCPBA or Oxone, and the resulting sulfoxide was treated under conditions of the Pummerer rearrangement, to give acetoxy sulfide and/or acetoxy acetal. Alkaline hydrolysis of the products provided the unprotected alcohols in good yields. Details of the reactions using several different substrates are described.

DIHYDRO 1,4-BENZOXAZINES AND METHOD OF SYNTHESIZING THE SAME USING SULFONIUM SALTS

Exemplary embodiments of the present invention relate to benzoxazines having various N-protecting groups. An R1 functional group is at least one selected from the group consisting of H and a halogen, an R2 functional group is at least one selected from the group consisting of H, an amide, or a carbamate, and a Z functional group is at least one selected from the group consisting of a phenyl, substituted phenyl group, methyl, and t-butyl group. The exemplary embodiments provide compounds with benzoxazines having various cleavable protecting groups such as amides and carbamates.

N-substituted phenoxazine and acridone derivatives: Structure-activity relationships of potent P2X4 receptor antagonists

P2X4 receptor antagonists have potential as drugs for the treatment of neuropathic pain and neurodegenerative diseases. In the present study the discovery of phenoxazine derivatives as potent P2X4 antagonists is described. N-Substituted phenoxazine and related acridone and benzoxazine derivatives were synthesized and optimized with regard to their potency to inhibit ATP-induced calcium influx in 1321N1 astrocytoma cells stably transfected with the human P2X4 receptor. In addition, species selectivity (rat, mouse, human) and receptor subtype selectivity (versus P2X1,2,3,7) were investigated. The most potent P2X4 antagonist of the present series was N-(benzyloxycarbonyl)phenoxazine (26, PSB-12054) with an IC50 of 0.189 μM and good selectivity versus the other human P2X receptor subtypes. N-(p-Methylphenylsulfonyl)phenoxazine (21, PSB-12062) was identified as a selective P2X4 antagonist that was equally potent in all three species (IC50: 0.928-1.76 μM). The compounds showed an allosteric mechanism of action. The present study represents the first structure-activity relationship analysis of P2X4 antagonists.

Amberlyst-15 catalyzed Cbz protection of amines under solvent-free conditions

Amberlyst-15 can effectively catalyze Cbz protection of aliphatic and aromatic amines within 10-15 min under solvent-free conditions. The catalyst can be used repeatedly without loss of activity, and the reaction requires no workup and gives excellent yields. Taylor & Francis Group, LLC.

An excellent method for Cbz-protection of amines

Cbz-protection of aliphatic and aromatic amines can be accomplished with benzylchloroformate using a catalytic amount of dodecatungstophosphoric acid hydrate (0.05 equiv). The reaction is simple, fast, does not require aqueous work-up and gives excellent yields.