89024-25-9

Upstream product

• 475273-35-9 N-(3,4-dimethoxyphenyl)methyl-N-methyl-cis-3-phenylsulfanylacrylamide 
• 475273-27-9 N-(3,4-dimethoxyphenyl)methyl-cis-3-phenylsulfanylacrylamide 
• 5219-65-8 acide phenylthio-3 propanoique 
• 108-98-5 thiophenol 
• 475273-20-2 p-nitrophenyl cis-3-phenylsulfanylacrylate 
• 706-01-4 (2Z)-3-(phenylthio)acrylic acid 
• 89024-23-7 N-Methyl-3-phenylsulfanylpropanamide 

Relevant academic research and scientific papers

Synthesis of 1,2-dihydrobenz[c]azepin-3-one via acid-catalyzed cyclization of N-arylmethyl-N-methyl-3-phenylsulfanylacrylamide

Treatment of N-arylmethyl-N-methyl-cis-3-phenylsulfanyl acrylamide (5) with p-toluenesulfonic acid induced two reactions; cyclization to 1,2-dihydrobenz[c]azepin-3-ones (7) and N-dearylmethylation to N-methylacrylamides (9 and 10) depending on the structu

Possible biomimetic synthesis of β-lactams

The first successful syntheses of β-lactams via a Pummerer rearrangement of the corresponding sulfoxides are described. Thus, variously substituted 3-(phenylsulfinyl)propionamides were converted to 4-(phenylthio)-2-azetidinones in 14-50% yields with trime

Formation of β-lactams from 3-phenylthiopropionamide derivatives. A possible model for penicillin biosynthesis

The Cu-catalysed reaction of the substituted 3-phenylthiopropianamide with di-t-butyl peroxide gives the β-lactam via oxidative cyclisation of the α-thioalkyl radical. Similar reactions of the propionamides with t-butyl perbenzoate give benzoates which can be readily converted into the β-lactams, but neither β-lactams nor benzoates can be obtained from the thiazepines. Dimethyl disulfide is benzoyloxylated on treatment with t-butyl perbenzoate. The relevance of these results to penicillin biosynthesis is discussed.