82264-40-2

Upstream product

• 917-64-6 methyl magnesium iodide 
• 73227-48-2 (2R,3R)-2-Methyl-1-oxy-3-phenyl-2,3-dihydro-azete-2-carboxylic acid diethylamide 
• 73227-46-0 (2R,3R)-2,4-Dimethyl-1-oxy-3-phenyl-2,3-dihydro-azete-2-carboxylic acid diethylamide 
• 78602-07-0 (cis)-N,N-diethyl-2,3-dihydro-2-methyl-3-phenyl-2-azetecarboxamide 1-oxide 

Downstream Products

• 73227-46-0 (2R,3R)-2,4-Dimethyl-1-oxy-3-phenyl-2,3-dihydro-azete-2-carboxylic acid diethylamide 
• 75909-31-8 N,N-diethyl-2,3-dihydro-2,4-dimethyl-3-phenyl-2-azetecarboxamide 1-oxide 
• 83152-74-3 3,5-dimethyl-4-phenyl-6H-1,2-oxazin-6-one 
• 83152-70-9 (2α,3α,4α)-N,N-diethyl-1-hydroxy-2,4-dimethyl-3-phenyl-2-azetidinemethanamine 
• 83152-77-6 2-<(diethylamino)methyl>-2,3-dihydro-2,4-dimethyl-3-phenylazete 1-oxide 
• 83152-73-2 (E)-N,N-diethyl-4-(hydroxyimino)-2-methyl-3-phenyl-2-pentenamide 
• 83152-71-0 (Z)-N,N-diethyl-4-(hydroxyimino)-2-methyl-3-phenyl-2-pentenamide 

Relevant academic research and scientific papers

Chemistry of Four-Membered Cyclic Nitrones. 3. Reaction with Nucleophilic Reagents and Stereospecific Conversion into 1-Hydroxyazetidines

Four-membered cyclic nitrones (1) react with a variety of nucleophiles (MeMgI, CN-, OH-, MeO-, and H-) by stereospecific addition to the C=N bond.Reaction of 1a with potassium cyanide and with methylmagnesium iodide yields the 1-hydroxyazetidines 2a and 2b, respectively.Reduction of 1b with lithium aluminum hydride and with sodium borohydride affords the 1-hydroxyazetidine derivatives 3 and 4, respectively.Sodium hydroxide in methanol-water reacts with 1a to give a mixture of two isomeric 5-hydroxyisoxazolidines 5a and 5b, but under similar reaction conditions 1b and 1c rearrange to the oximes 6 and 7.In acetic acid at room temperature 6a cyclizes to the 6H-1,2-oxazin-6-one derivative 8, whereas 6b yields 5-methyl-3,4-diphenylisoxazole (9) after being refluxed in acetic acid, probably by carbon monoxide elimination from the intermediate oxazin-6-one derivative.Reaction of 1a with sodium hydroxide for 2 min gives exclusively the 1-hydroxy-4-methoxyazetidine 13a, whereas prolonged reaction gives the isomeric azetidine 13b together with 5 (mixture of 5a and 5b in a ratio 4:1).Single-crystal X-ray analysis of 13b reveals that all three relatively bulky substituents at C-2, C-3, and C-4 are on the same face of the azetidine ring.Treatment of 13b with acetic acid at room temperature gives the 5-methoxyisoxazolidine 15.The 1-hydroxyazetidines 2-4 are oxidized with yellow mercury(II) oxide to the corresponding four-membered cyclic nitrones 1b, 16 and 17.

OXIDATION OF N-HYDROXYAZETIDINES: A NOVEL SYNTHESIS OF N-ACETOXY β-LACTAMS AND FOUR-MEMBERED CYCLIC NITRONES

The N-hydroxyazetidines 2 and 3 are prepared starting from 2,3-dihydroazete 1-oxides (1a and 1b) by reduction with sodium borohydride and by reaction with a nucleophile, respectively.The N-hydroxyazetidines 2 and 3 can be oxidized with mercury(II)oxide to