119492-93-2

Upstream product

• 33692-63-6 dimethyl N-(para-methoxyphenyl)-dithio-carbonimidate 
• 122-59-8 2-phenoxyacetic acid 
• 701-99-5 Phenoxyacetyl chloride 

Downstream Products

• 119492-99-8 1-(4-Methoxy-phenyl)-3-phenoxy-azetidin-2-one 
• 142389-10-4 1-(4-methoxyphenyl)-3-phenoxyazetidine-2,4-dione 
• 946069-58-5 1-(4'-methoxy-phenyl)-3-phenoxy-4,4-bis(methylsulfonyl)azetidin-2-one 
• 1294450-10-4 carbamoyl-phenoxy-thioacetic acid S-methyl ester 
• 1294450-11-5 4,4-bis(methylsulfonyl)-1-(4-methoxy-3-nitro-phenyl)-2-phenoxy-azetidin-2-one 

Relevant academic research and scientific papers

4,4-Bis(methylthio)azetidin-2-ones as synthons of 1,2- and 1,3-dicarbonyl systems

The importance of β-lactams as synthetic building blocks has been widely recognized in organic synthesis due to possible ring cleavage at any of the four single bonds of the β-lactam ring. We now report reactions involving breaking of the N1-C4 bond in differently substituted at C3 4,4-bis(methylthio)azetidin-2-ones, leading to formation of 1,2- and 1,3-dicarbonyl systems.

Triphosgene: A versatile reagent for the synthesis of azetidin-2-ones

An efficient use of triphosgene, as an acid activator, for the synthesis of substituted azetidin-2-ones via ketene-imine cycloaddition reaction using various acids and imines have been described.

A facile synthesis of azetidine-2,4-diones

Azetidine-2,4-diones 6 can be conveniently synthesized by mild oxidative hydrolysis of 4,4-bis(alkylthio)azetidin-2-ones 5 using N-bromosuccinimide.

Synthesis of 4-Unsubstituted β-Lactams via Dithiocarbonimidates

Cycloaddition of dithiocarbonimidate 1 to the ketene generated in situ from phenoxyacetylchloride in the presence of triethylamine affords the 4-dithioalkyl-2-azetidinones 2 in good yields.Facile conversion of 2 to the 4-unsubstituted β-lactams 3 can be accomplished by desulfurization with Raney-Nickel.Formation of several interesting products during attempts to bring a carbonyl function at C-4 in 2 has also been described.