115142-72-8

Upstream product

• 104-94-9 4-methoxy-aniline 
• 108908-63-0 N-4-methoxyphenyl-α-methylcinnamylideneamine 
• 122-59-8 2-phenoxyacetic acid 
• 108908-71-0 cis-1-(4-methoxyphenyl)-4-(α-methylstyryl)-3-phenoxy-2-azetidinone 

Downstream Products

• 119492-99-8 1-(4-Methoxy-phenyl)-3-phenoxy-azetidin-2-one 
• 115142-77-3 cis-4-acetoxy-1-(4-methoxyphenyl)-3-phenoxy-2-azetidinone 

Relevant academic research and scientific papers

Base-promoted isomerization of cis-4-formyl-2-azetidinones: Chemoselective C4-epimerization vs rearrangement to cyclic enaminones

Two simple, efficient, and complementary methods for the regiospecific C4-epimerization of cis-4-formyl-2-azetidinones 1-3 are described. The first method uses 40% aqueous dimethylamine as reagent in heterogeneous medium with benzene at room temperature, in the presence of benzyltributylammonium bromide (3-4 mol %) as the phase-transfer catalyst. This transformation tolerates alkyl, alkenyl, alkynyl, aryl, and alkoxy substituents at the C3 of the 2-azetidinone ring. However, limitations of this isomerization are as follows: (i) only N-(p-methoxyphenyl)-β-lactams can be used, and (ii) transformation is less compatible with heteroatomic substituents bonded to the C3 position of the 2-azetidinone ring. A highly general solution to these problems relies on the use of sodium carbonate as the isomerization reagent in different solvents. We also describe a novel base-promoted rearrangement of the β-lactam ring to cyclic enaminones 6 and 21, involving an E1cB-elimination reaction in cis-4-formyl-2-azetidinones.

Preparation of 4-Unsubstituted β-Lactams from 4-Acetoxyazetidin-2-ones.A Formal Approach to Monobactams and Nocardicins

The synthesis of 4-unsubstituted azetidin-2-ones is described.Treatment of Schiff bases derived from α-methylcinnamaldehyde and amines with acetic acids in the presence of phenyl dichlorophosphate and triethylamine followed by ozonolysis of the resulting