97651-37-1

Upstream product

• 1250901-32-6 N-methoxy-N-methyl-N²-phenylglycinamide 
• 103-01-5 N-Phenylglycine 
• 593-71-5 Chloroiodomethane 
• 1444623-82-8 N-methoxy-N-methyl-N²-[(4-methylphenyl)sulfonyl]-N²-phenylglycinamide 
• 80271-13-2 N-tosyl-N-phenylglycyl chloride 
• 97651-42-8 N-(3-diazo-2-oxopropyl)-N-phenyl-4-methylbenzenesulphonamide 
• 186581-53-3 diazomethane 

Relevant academic research and scientific papers

Chemoselective synthesis of N-substituted α-amino-α′- chloro ketones via chloromethylation of glycine-derived Weinreb amides

Functionalized α-arylamino-α′-chloro ketones are obtained in high yield via a straightforward homologation reaction of Weinreb amides derived from N-arylglycines using in situ generated chloromethyllithium. The use of the Weinreb amides is essential and allows the chemoselective homologation of N-aryl-N-substituted glycine analogues, a transformation which is not possible using similar glycine esters. The procedure is promising for the large-scale preparation of α-amino-α′-chloropropanones, which are valuable precursors for a variety of bioactive compounds. Copyright

ACETOLYSIS OF α'-SULPHONAMIDO α-CHLORO AND α-DIAZO KETONES. A CONVENIENT SYNTHESIS OF 3-AZETIDINONES

Acetolysis of tertiary sulfonyl amides 1b,d leads to chlorine cinesubstitution exclusively, while in the case of the secondary amides 1a,c,e, only products of β-elimination are obtained.Acetolysis of the related diazo ketones 2b,d bearing a tertiary nitrogen atom, leads to normal substitution of the diazo group exclusively, whereas with the corresponding secondary amides 2a,c,e a concurrent cyclization to the 3-azetidinones 9, 12 and 15 is observed.By decomposition of the same diazoketones 2a,c,e in the presence of catalytic amounts of Cu(CF3COCHCOCF3)2, the above 3-azetidinones are obtained in excellent yields.