89024-23-7

Upstream product

• 591-51-5 phenyllithium 
• 1003-22-1 2-methyl-isothiazolidin-3-one 
• 5219-65-8 acide phenylthio-3 propanoique 
• 74-89-5 methylamine 
• 108-98-5 thiophenol 

Downstream Products

• 89024-24-8 3-benzoyloxy-N-methyl-3-(phenylthio)propionamide 
• 89024-25-9 N-methyl-cis-3-phenylsulfanylacrylamide 
• 68960-65-6 1-methyl-4-phenylthioazetidin-2-one 

Relevant academic research and scientific papers

SYNTHESES OF β-LACTAMS BY RING CONTRACTION OF ISOTHIAZOLIDINONES

Several methods have been developed for the preparation of β-lactams from isothiazolidinones.Oxidation of 2-t-butyl-4,4-diphenyl- and 2,4,4-trimethyl-isothiazolidin-3-ones (4a) and (4b) with sulphuryl chloride afforded the 5-chloroisothiazolidinones (5a) and (5b), which were converted into 1-t-butyl-3,3-diphenyl- nd 1,3,3-trimethyl-4-phenylthioazetidin-2-ones (6a) and (6b) by treatment with phenyl-lithium.Alternatively, reaction of the isothiazolidinones (4a) and (4b) with phenyl-lithium gave N-t-butyl-2,2-diphenyl- and N,2,2-trimethyl-3-phenylthiopropionamides(12a) and (12b), which were transformed into the β-lactams (6a) and (6b) by halogenation at C-3, followed by treatment with potassium amide.These are examples of methods used to prepare β-lactams from isothiazolidinones.The verstility of these reactions and their relevance to penicilin biosynthesis is discussed.

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.