16172-23-9

Upstream product

• 75-15-0 carbon disulfide 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 100-52-7 benzaldehyde 
• 90985-86-7 phenylthio(trimethylsilyl)methyl isothiocyanate 
• 40046-25-1 Phenacyl isothiocyanate 
• 58417-70-2 5-hydroxy-5-phenyl-thiazolidine-2-thione 

Downstream Products

• 57203-38-0 2-(4-nitro-phenylsulfanyl)-5-phenyl-oxazole 
• 135307-33-4 N,5-diphenyloxazol-2-amine 
• 62124-43-0 2-Chloro-5-phenyloxazole 
• 140685-64-9 2-cinnamylthio-5-phenyloxazole 
• 140685-85-4 2-benzylthio-5-phenyloxazole 
• 25444-98-8 3-methyl-5-phenyl-3H-oxazole-2-thione 

Relevant academic research and scientific papers

A convenient synthesis of 2-mercapto-oxazoles via β-ketoazide and its application to a key intermediate of PI3Kγ inhibitors

A convenient synthesis of 2-mercapto-oxazoles via the reaction of β-ketoazide with triphenylphosphine (TPP) and carbon disulfide and its application to the synthesis of a key intermediate of phosphoinositide 3-kinase γ (PI3Kγ) inhibitors are described. The Japan Institute of Heterocyclic Chemistry.

Discovery and evaluation of 2-anilino-5-aryloxazoles as a novel class of VEGFR2 kinase inhibitors

A series of derivatives of 2-anilino-5-phenyloxazole (5) has been identified as inhibitors of VEGFR2 kinase. Herein we describe the structure-activity relationship (SAR) of this novel template. Optimization of both aryl rings led to very potent inhibitors at both the enzymatic and cellular levels. Oxazole 39 had excellent solubility and good oral PK when dosed as the bis-mesylate salt and demonstrated moderate in vivo efficacy against HT29 human colon tumor xenografts. X-ray crystallography confirmed the proposed binding mode, and comparison of oxazoles 39 and 46 revealed interesting differences in orientation of 2-pyridyl and 3-pyridyl rings, respectively, attached at the meta position of the 5-phenyl ring.

Chloro(phenylthio)methyltrimethylsilane: Preparation and some Synthetic Reactions

Reaction of the title compound (2) with lead thiocyanate gave phenylthio(trimethylsilyl)methyl isothiocyanate (3) which further reacted with aromatic aldehydes in the presence of fluoride ion to afford oxazoles in good yields.Compound (2) also reacted with silyl enol ethers to give β-silyl ketones which were capable of being converted into β-functionalized vinylsilanes.

SYNTHESIS AND STABILITY OF 2-OXOISOTHIOCYANATES

Enolizable 2-oxoisothiocyanates Ia-If were prepared from hydrochlorides of amino ketones, containing a hydrogenatom in the α-position, by reaction with thiophosgene in the presence of CaCO3.At room temperature the enol form of these compounds undergoes slow cyclization to give the isomeric 4-oxazoline-2-thiones IIb-IIf.In the presence of bases this isomerization proceeds rapidly even at room temperature. 2-Isothiocyanatocyclopentanone (Ia) does not cyclize to the corresponding oxazolinethione either on heating or action of bases.The rate of the thermally initiated isomerization of the 2-oxoisothiocyanates Ib-If was determined by IR spectroscopy.