16735-28-7

Upstream product

• 637-50-3 1-phenylpropene 
• 4962-45-2 2-bromo-1-phenyl-propan-1-ol 
• 93-55-0 1-phenyl-propan-1-one 
• 108-24-7 acetic anhydride 
• 16735-19-6 2-amino-1-phenylpropan-1-one hydrochloride 
• 119-51-7 1-phenyl-1,2-propanedione 2-oxime 
• 3509-76-0 (+/-)-N-acetylnorephedrine 
• 3509-76-0 N-((1RS,2RS)-2-hydroxy-1-methyl-2-phenyl-ethyl)-acetamid; N-acetyl-dl-norpseudoephedrine 

Downstream Products

• 16735-19-6 2-amino-1-phenylpropan-1-one hydrochloride 
• 41940-17-4 3,5-dimethyl-6-phenyl-[1,2,4]triazine 
• 556826-66-5 (+/-)-N-(propiophenone-2-yl)-2',3'-diethoxycarbonyl-1'-propylamine 
• 54600-85-0 2,5-dimethyl-3,6-diphenylpyrazine 
• 19968-55-9 2,4-dimethyl-5-phenylthiazole 
• 23012-31-9 2,4-dimethyl-5-phenyloxazole 
• 3509-76-0 (+/-)-N-acetylnorephedrine 
• 3509-76-0 N-((1RS,2RS)-2-hydroxy-1-methyl-2-phenyl-ethyl)-acetamid; N-acetyl-dl-norpseudoephedrine 
• 110196-19-5 3,5-dimethyl-6-phenyl-4,5-dihydro-[1,2,4]triazine 

Relevant academic research and scientific papers

Pyrrolo[2,1-d][1,2,3,5]tetrazine-4(3H)-ones, a new class of azolotetrazines with potent antitumor activity

Pyrrolo[2,1-d][1,2,3,5]tetrazinones 10a-o, compounds that hold the deaza skeleton of the antitumor drug temozolomide, were prepared by reaction of 2-diazopyrroles 9 and isocyanates. Such a synthetic route represents, among those leading to azolotetrazinones reported so far, the only possible one since attempts to cyclize to the title ring system 2-amino-1-carbamoylpyrroles 11 or the mono substituted 2-triazenopyrrole 12 failed. Compounds 10 were screened at the National Cancer Institute (NCI) for their activity against a panel of about 60 human tumor cell lines. Most of them possess remarkable antineoplastic activity having GI50 values in the low micromolar or sub-micromolar range and reaching, in the case of compound 10d, nanomolar concentrations. The most sensitive cell lines were MDA-N and MDA-MB-435 of the breast sub-panel, and SR, K-562, HL60 (TB) and CCRF-CEM of the leukaemia sub-panel. SAR evaluation and COMPARE computations indicate, for compounds 10, a mechanism of action different from that of temozolomide.

Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones

The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with the liberation of N2 followed by intramolecular migration of the acyl moiety. A wide range of α-amido ketones were obtained, and one-pot transformation into the corresponding oxazoles (or a thiazole) was demonstrated.

Chemistry of indoles carrying a basic function. Part VII. A new aspect of Stobbe reaction

While performing Stobbe reactions of a succinic diester derivative (1) different routes were found leading to different indole derivatives (2-5) depending on the reaction conditions applied, thus widening the scope and limitation of this useful procedure. Simpler pyrrolidine (13) and piperidine derivatives (14, 15) were also achieved through application of the intramolecular Stobbe reaction.

Indium metal as a reducing agent in organic synthesis

The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. The use of indium metal for the reduction of C=N bonds in imines, the heterocyclic ring in benzo-fused nitrogen heterocycles, of oximes, nitro compounds and conjugated alkenes and the removal of 4-nitrobenzyl protecting groups is described. Thus the heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanolic ammonium chloride. Treatment of a range of aromatic nitro compounds under similar conditions results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected. Likewise indium in aqueous ethanolic ammonium chloride is an effective method for the deprotection of 4-nitrobenzyl ethers and esters. Indium is also an effective reducing agent under non-aqueous conditions and α-oximino carbonyl compounds can be selectively reduced to the corresponding N-protected amine with indium powder, acetic acid in THF in the presence of acetic anhydride or di-tert-butyl dicarbonate. Conjugated alkenes are also reduced by indium in THF-acetic acid.

Indium as a reducing agent: Reduction of oximes

α-Oximino carbonyl compounds can be selectively reduced to the corresponding N-acetyl amine with indium powder, acetic anhydride and acetic acid in THF.