82865-29-0

Upstream product

• 16446-29-0 2-phenyl-3-thiazolin-5-one 
• 100-52-7 benzaldehyde 
• 507-09-5 thioacetic acid 
• 17606-70-1 (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one 
• 1892-31-5 thiopropionic acid 
• 6330-48-9 thiohippuric acid 
• 15732-43-1 (E)-2-phenyl-4-benzylidene-5(4H)-oxazolone 
• 623-33-6 glycine ethyl ester hydrochloride 
• 199447-37-5 4,4'-Dibenzyl-2,2'-diphenyl-4H,4'H-[4,4']bithiazolyl-5,5'-dione 
• 613-94-5 benzoic acid hydrazide 
• 22963-07-1 4-benzyl-2-phenylthiazol-5(4H)-one 
• 2584-64-7 N-(thiobenzoyl)glycine 
• 5873-86-9 methyl thiobenzoate 
• 22962-97-6 4-methyl-2-phenylthiazolone 

Downstream Products

• 86557-65-5 4,4'-bi-<2-phenyl-4-(2-phenylallyl)5(4H)-thiazolone> 
• 4525-05-7 (E)-1,5-diphenyl-7-oxo-6-thia-4-azaspiro<2.4>hept-4-ene 
• 4525-05-7 (Z)-1,5-diphenyl-7-oxo-6-thia-4-azaspiro<2.4>hept-4-ene 
• 128870-83-7 4,7-Diphenyl-3-(2,4,6-trimethyl-phenyl)-1-oxa-8-thia-2,6-diaza-spiro[4.4]nona-2,6-dien-9-one 
• 128901-00-8 3-(4-Chloro-phenyl)-1,4,7-triphenyl-8-thia-1,2,6-triaza-spiro[4.4]nona-2,6-dien-9-one 
• 128870-85-9 3-(2,6-Dichloro-phenyl)-4,7-diphenyl-1-oxa-8-thia-2,6-diaza-spiro[4.4]nona-2,6-dien-9-one 
• 82865-30-3 2,5-diphenyl-2-thiazoline-4-carboxylic acid 
• 82865-31-4 methyl trans-2,5-diphenyl-2-thiazoline-4-carboxylate 
• 82865-32-5 N-(trans-2,4-diphenyl-2-thiazolin-5-ylcarbonyl)glycylproline 
• 128870-94-0 Methyl 3-mesityl-4-phenyl-5-isoxazolecarboxylate 
• 128870-98-4 1,3,4-Triphenyl-5-(thiobenzoylamino)pyrazole 
• 128870-95-1 4,5-Dihydro-3-mesityl-4-phenyl-5-(thiobenzoylamino)-5-isooxazolecarboxylic acid 
• 128870-93-9 4,5-Dihydro-3-mesityl-4-phenyl-5-(thiobenzoylamino)-5-isoxazolecarboxylate 
• 128870-97-3 Methyl 4,5-dihydro-1,3,4-triphenyl-5-(thiobenzoylamino)-5-pyrazolcarboxylate 

Relevant academic research and scientific papers

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.

Improved erlenmeyer synthesis with 5-thiazolone and catalytic Mn(II) acetate. Crystal structure confirmation of the reaction stereochemistry

2-Phenylthiazolin-5-one (5, a thioazlactone) condenses with various aldehydes in the presence of the mild base Mn(II) acetate as catalyst in CH 2Cl2 solution. This leads to the corresponding Erlenmeyer reaction products (6) in excell

Synthesis of symmetrical 2,2′,4,4′-tetrasubstituted [4,4′-bithiazole]-5,5′(4H,4′H)-diones and their reactions with some nucleophiles

Symmetrical ,2′,4,4′-tetrasubstituted-[4,4′-bithiazole]-5,5′(4H, 4′H)-diones were obtained in high yields by oxidation of 5(4H)-thiazolones by KMnO4 in acetic acid. In some cases, the isomeric 2,4′- and 2,2′-bithiazolones were also formed. Results from two crossover reactions were consistent with a free radical mechanism. Four series of thiazolones were prepared, each based on a different substituent at the 2-position; i.e., phenyl, ethoxy, ethyl and ethylthio. The effects of substituents on the isomer distributions of the dehydrodimers indicated that electronic factors were less important than steric factors. X-Ray crystallography established the structure of the dehydrodimer (4R*,4′R*)-2,2′-diethoxy-4,4′-dibenzyl-[4,4′ -bithiazole]-5,5′(4H,4′H)-dione. One stereoisomer of 2,2′-diphenyl-4,4′-dimethyl-[4,4′-bithiazole]-5,5′(4H, 4′H)-dione and a mixture of the stereoisomers of 2,2′ -diphenyl-4,4′-dibenzyl-[4,4′-bithiazole]-5,5′(4H,4′H)- dione were treated with nucleophiles. The former gave imide derivatives of ,′-dehydrodimeric amino acids when the nucleophile was L-alanine ethyl ester or 1-butylamine. The structure of one of the reaction products, (4R*,5R*)-2,5-diphenyl-2-thiazoline-4-carboxylic acid piperidylamide, was established by X-ray crystallography. Treatment of stereoisomeric mixtures of 2,2′-diethoxy-4,4′-bithiazolones with HCl in benzene gave the corresponding racemic and meso bis-(N-carboxythioanhydride)s. A stereoisomeric mixture of the bis(N-carboxythioanhydride)s of leucine treated with glycine ethyl ester gave a bicyclic derivative of the ,′-dehydrodimeric amino acid. Acta Chemica Scandinavica 1997.

REACTION OF 5(4H)-THIAZOLONES WITH DIAZOMETHANE

The reaction of diazomethane with several (Z)-2-substituted-4-benzylidene-5(4H)thiazolones (1) (2-substitution: SCH2Ph, OCH2Ph, SCH3, CH3, Ph), under two different conditions, has been studied.In benzene at 45 deg C (Z) and (E)-2-substituted-1-phenyl-7-ox