84757-15-3

Upstream product

• 6780-38-7 N-phthaloylglycine chloride 
• 538-51-2 benzylidene phenylamine 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 4702-13-0 N-phthaloylglycine 
• 33993-35-0 cis-benzylideneaniline 
• 69177-79-3 Phthalimido-keten 

Downstream Products

• 78942-01-5 3-Benzylideneamino-1,4-diphenyl-2-azetidinone 
• 16342-61-3 (+/-)-trans-3-amino-1,4-diphenylazetidin-2-one 

Relevant academic research and scientific papers

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

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

Reactions of acid chlorides/ketenes with 2-substituted 4,5-dihydro-4,4- dimethyl-1,3-thiazoles: Formation of penam derivatives

Addition reactions of acid chlorides with various 2-substituted 4,5-dihydro-4,4-dimethyl-5-(methylsulfanyl)-1,3-thiazoles under basic conditions were studied. Two kinds of products were obtained from these additions, β-lactams and non-β-lactam adducts. When the reaction was carried out with 4,5-dihydro-1,3-thiazoles with a Ph substituent at C(2), the reaction proceeded via formal [2+2] cycloaddition and led to the correspoding β-lactam. On the other hand, acid chlorides and 4,5-dihydro-1,3-thiazoles bearing an α-H-atom at the C(2)-substituent underwent C(α)- and/or N-addition reactions and furnished non-β-lactam adducts, i.e., C(α)- and/or N-acylated 1,3-thiazolidines. The attempted transformations of sulfonyl esters of exo-6-hydroxy penams to endo-6-azido penams failed, although they were successful with mono-β-lactams under the same conditions. Copyright

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

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).

Reagents and Synthetic Methods. Part 58. Synthesis of β-Lactams from Acetic Acids and Imines promoted by Vilsmeier Type Reagents

The development of a practical method for the stereospecific preparation of several 3-substituted β-lactams from acetic acids and imines is described.The key step of the method is the activation of the carboxy component by means of Vilsmeier type reagents.The preparation of some N-(2'-hydroxyethyl)-β-lactams and N-(p-dimethyl-t-butylsiloxyphenyl)-β-lactams as intermediates for N-H azetidinones is also reported.For the last compounds the steric bulk of the N-substituent is the key feature for a high cis-β-lactam formation.

TRIPHENYLPHOSPHINE DIBROMIDE AND DIMETHYLSULFIDE DIBROMIDE AS VERSATILE REAGENTS FOR BETA-LACTAM SYNTHESIS

Triphenylphosphine dibromide and dimethylsulfide dibromide are efficient reagents for the direct synthesis of beta-lactams from carboxylic acids and imines avoiding the use of acid halides as starting materials.Synthesis of 4-imino-beta-lactams are also briefly described.A potential synthesis of N-unsubstituted beta-lactams is made.

N,N-DIMETHYLCHLOROSULFITEMETHAMINIUM CHLORIDE (SOCl2-DMF) A VERSATILE DEHYDRATING REAGENT.

N,N-dimethylchlorosulfitemethaminium chloride formed from thionyl chloride and dimethylformamide was found and efficient reagent for the synthesis of acyl azides from carboxylic acids and nitriles from oximes.It is also highly efficient for the direct synthesis of beta-lactams from carboxylic acids and imines avoiding the use of acid chlorides.