16342-61-3

Upstream product

• 19018-08-7 (+/-)-trans-1,4-diphenyl-2-oxo-4-phenylazetidin-3-yl-isoindoline-1,3-dione 
• 94615-16-4 (2R,3R)-2,3-Dimethoxy-N-((3R,4R)-2-oxo-1,4-diphenyl-azetidin-3-yl)-succinamic acid methyl ester 
• 94615-14-2 (3R,4R)-3,4-Dimethoxy-1-((3R,4R)-2-oxo-1,4-diphenyl-azetidin-3-yl)-pyrrolidine-2,5-dione 
• 538-51-2 benzylidene phenylamine 
• 62-53-3 aniline 
• 100-52-7 benzaldehyde 
• 19018-08-7 N-(2-oxo-1,4-diphenyl-azetidin-3-yl)-phthalimide 
• 70208-18-3 (E)-3-((3S,4R)-2-Oxo-1,4-diphenyl-azetidin-3-ylamino)-but-2-enoic acid ethyl ester 

Downstream Products

• 16876-72-5 (R)-2-amino-N,3-diphenyl-propanamide 
• 142581-42-8 (3RS,4SR)-(+/-)-3-<(5rs)-3,4-Dichlor-2,5-dihydro-5-methoxy-2-oxo-1H-pyrrol-1-yl>-1,4-diphenylazetidin-2-on 
• 142581-46-2 (3RS,4SR)-(+/-)-<(5RS)-3,4-Dichlor-2,5-dihydro-5-hydroxy-2-oxo-1H-pyrrol-1-yl>-1,4-diphenylazetidin-2-on 
• 142581-46-2 (3RS,4SR)-(+/-)-3-<(5SR)-3,4-Dichlor-2,5-dihydro-5-hydroxy-2-oxo-1H-pyrrol-1-yl>-1,4-diphenylazetidin-2-on 
• 34092-17-6 3-benzoylamino-1,4-diphenylazetidin-2-one 
• 78942-01-5 3-Benzylideneamino-1,4-diphenyl-2-azetidinone 

Relevant academic research and scientific papers

Microwave-induced bismuth nitrate-catalyzed Michael reaction of 3-amino β-lactams with enones

Microwave-induced bismuth nitrate-catalyzed reaction of 3-amino β-lactams with unsaturated ketones is performed in order to obtain substituted amino β-lactams. Amino β-lactams were obtained through the strategy of [2+2] ketene-imine cycloaddition followed

A green, chemoselective, and practical approach toward N-(2-azetidinonyl) 2,5-disubstituted pyrroles

Pyrrole and 2-azetidinone are two essential heterocyclic scaffolds, which are being broadly used in medicinal chemistry and drug discovery field. A green and practical method to synthesize novel N-(2-azetidinonyl) 2,5-disubstituted pyrroles, which are com

Novel synthesis of 3-pyrrole substituted β-lactams via microwave-induced bismuth nitrate-catalyzed reaction

Highly stereoselective synthesis of 3-pyrrole substituted β-lactams is accomplished. The first step involves the synthesis of 3-phthalimido substituted β-lactams following Staudinger cycloaddition reaction of acid chloride equivalent with imines. Synthesi

Synthesis of structurally diverse 2-azetidinones via staudinger reaction on a solid support

Trimellitic anhydride was attached to Merrifield resin and a ketene was generated from polymer-bound phthaloylglycine. Then this polymer reacted with imines in the presence of Vilsmeier reagent and triethylamine to afford the solid-phase-tethered β-lactam products. Selective cleavage of supported β-lactams by trifluoroacetic acid and methylhydrazine gave 4-carboxyphthalimido- and 3-amino-β-lactams, respectively. The trans-stereochemistry was found in all products.

Remarkable iodine-catalyzed synthesis of novel pyrrole- bearing n-polyaromatic β-lactams

Because of their interesting biological properties various methods for the synthesis of substituted pyrroles are described in the literature. However, synthesis of pyrroles fused with a β-lactam ring has not been reported. Our group has demonstrated synth

N,N-dibenzyloxycarbonylglycyl chloride as useful ketene equivalent in the synthesis of azetidin-2-ones

N,N-3-Dibenzyloxycarbonylaminoazetidin-2-ones have been conveniently prepared from N,N-dibenzyloxycarbonylglycyl chloride and imines or hexahydrotriazines. The β-lactams thus obtained could be monodeprotected by mild hydrogenolysis with Pd on carbon.

Acid-aided reactions of 3-acylamino-β-lactams: Some observations

3-Benzoylamino-1,4-diphenylazetidin-2-one (1a) gives 2-benzoylaminocinnamanilide (3a) and 4-benzylidene-1,2-diphenylimidazolin-5-one (4a) when heated in gl. acetic acid containing conc.H2SO4. 3-Acetylaminoazetidin-2-one (1b) forms tar under similar conditions, but in the presence of benzaldehyde it affords 2-cinnamoylaminocinnamanilide (3c) and 4-benzylidene-2-styryl-2-imidazolin-5-one (4c). 3-(2-Benzoylaminocinnamoylamino)-1,4-diphenylazetidin-2-one (1c), on the other hand furnishes 4-benzylidene-2-phenyl-2-oxazolin-5-one (2a) and 3-amino-1,4-diphenylazetidin-2-one (14).Mechanisms are given.

β-Lactams and β-lactam-intermediates, II: Stereoselective synthesis of cis-3-amino-1,4-diphenyl-azetidin-2-one

Phthalylglycyl chloride (1) reacts with benzalaniline (3) in the presence of triethylamine to yield 1,4-diphenyl-3-phthalimido-azetidin-2-one (5). The selectivity of formation of cis-β-lactam 5 was improved considerably by decreasing the concentration of chloride in the reaction-solution and by lowering of the temperature. Hydrazinolysis of 5 yields 3-amino- 1,4-diphenyl-azetidin-2-one (8).

SYNTHETIC STUDIES ON OPTICALLY ACTIVE β-LACTAMS. ASYMMETRIC SYNTHESIS OF β-LACTAMS BY THE CYCLOCONDENSATION UTILIZING CHIRAL HETEROCYCLIC COMPOUNDS DERIVED FROM L-(+)-TARTARIC ACID AND (S)-GLUTAMIC ACID

Asymmetric cyclocondensation of the chiral heterocyclic compounds (2,4) with imines (5) gave either cis- or trans-β-lactams with high diastereomeric purity up to 96percent, and the optically pure phenylalanine derivative (9) was obtained from the β-lactams produced.

Unambiguous Synthesis of 3-Benzoylamino-3-methyl-1,4-diphenyl-2-azetidinone

3-Methyl-1,4-diphenyl-3-phthalimido-2-azetidinone (5b), obtained by the reaction of phthaloylalaninyl chloride (1b) with benzylideneaniline in the presence of triethylamine, has been converted into the title compound (12) via its amino analogue (11).