128870-92-8

Basic information

• Product Name: 4-((Z)-4-methyl-benzylidene)-2-phenyl-4H-thiazol-5-one
• CAS NO: 128870-92-8
• Molecular Weight: 279.362
• Mol File: 128870-92-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-((Z)-4-methyl-benzylidene)-2-phenyl-4H-thiazol-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((Z)-4-methyl-benzylidene)-2-phenyl-4H-thiazol-5-one(128870-92-8)
• EPA Substance Registry System: 4-((Z)-4-methyl-benzylidene)-2-phenyl-4H-thiazol-5-one(128870-92-8)

Safety Data

• Hazardous Substances Data: 128870-92-8(Hazardous Substances Data)

Upstream product

• 57427-79-9 (Z)-4-(4-methylbenzylidene)-2-phenyloxazol-5(4H)-one 
• 2584-64-7 N-(thiobenzoyl)glycine 
• 5873-86-9 methyl thiobenzoate 
• 16446-29-0 2-phenyl-3-thiazolin-5-one 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 128870-86-0 3-(2,6-Dichloro-phenyl)-7-phenyl-4-p-tolyl-1-oxa-8-thia-2,6-diaza-spiro[4.4]nona-2,6-dien-9-one 
• 128870-90-6 1,7-Diphenyl-3,4-di-p-tolyl-8-thia-1,2,6-triaza-spiro[4.4]nona-2,6-dien-9-one 
• 128870-88-2 1,3,7-Triphenyl-4-p-tolyl-8-thia-1,2,6-triaza-spiro[4.4]nona-2,6-dien-9-one 
• 128870-84-8 7-Phenyl-4-p-tolyl-3-(2,4,6-trimethyl-phenyl)-1-oxa-8-thia-2,6-diaza-spiro[4.4]nona-2,6-dien-9-one 

Relevant articles and documents

Reactivity of (Z)-4-Aryliden-5(4 H)-thiazolones: [2 + 2]-Photocycloaddition, Ring-Opening Reactions, and Influence of the Lewis Acid BF3

The irradiation of (Z)-2-phenyl-4-aryliden-5(4H)-thiazolones 2 with blue light (465 nm) in CH2Cl2 solution promotes [2 + 2]-photocycloaddition of the exocyclic C═C bonds and the formation of the dispirocyclobutanes 3. This reaction takes place with high stereoselectivity, given that the ?-isomer (1,3 head-to-tail syn coupling) is formed in more than 90% yield in most of the cases. However, irradiation of 5(4H)-thiazolones 2 with blue light (456 nm) in dry MeOH in the presence of BF3·OEt2 leads to the monospirocyclobutanes 4 with full stereoselectivity, also affording the ?-isomer. A ring-opening reaction of only one of the thiazolone rings appears to have taken place in 4 upon methanolysis, leading to the corresponding ester and thioamide groups. The treatment of free 4-aryliden-5(4H)-thiazolones 2 with a base in alcohol (NaOR/ROH) also produces a ring-opening reaction of the heterocycle by methanolysis, although, under these reaction conditions, further intramolecular S-attack at the exocyclic C(H)═C bond and cyclization is observed, forming the dihydrothiazoles 5 or 6 as mixtures of cis (RS/SR)- and trans (RR/SS)-isomers with high diastereomeric excess. trans-(RR/SS)-Dihydrothiazoles 6 can be isolated as pure diastereoisomers by column chromatography. Surprisingly, dihydrothiazoles 5 can also be obtained by the treatment of 4-aryliden-5(4H)-thiazolones 2 with BF3·OEt2 in methanol in the absence of a base.