33812-89-4Relevant academic research and scientific papers
Microwave-induced cycloaddition of imines with acid chlorides in absence of a tertiary amine: Unprecedented synthesis of β-lactams in dimethylformamide
Yadav, Ram Naresh,Chavez, Ashlee,Banik, Bimal Krishna
, p. 1365 - 1367 (2020/06/27)
Synthesis β-lactams in N,N-dimethylformamide proceeds through cycloaddition of acid chlorides with imines in a domestic microwave oven in the absence of a tertiary base. This is an unprecedented observation.
Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity
Walsh,Meegan,Prendergast,Al Nakib
, p. 989 - 1000 (2007/10/03)
The synthesis of a series of 3-acetoxyazetidin-2-ones 3a-n and 3-hydroxyazetidin-2-ones 6a-j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a-h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substituted Schiff bases 10a-h with acetoxyacetyl chloride. The novel bicyclic structures 7-acetoxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and 7-hydroxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtained. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candida albicans, Candida tropicalis, Candida parapsilosis, Candida glabrata, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a-h containing a free carboxylic acid group on the N-1 aryl ring displayed antibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Escherischia coli.
Cycloadditions of (Alkylarylamino)ketenes with Imines. cis-3-Amino-2-azetidinones
Brady, William T.,Gu, Yi Qi
, p. 2838 - 2842 (2007/10/02)
The in situ cycloaddition of (alkylarylamino)ketenes with various imines to form predominately cis-3-amino-2-azetidinones is described.A mechanism involving a dipolar intermediate is provided whereby the structure of the intermediate is determined by both
TRIPHENYLPHOSPHINE DIBROMIDE AND DIMETHYLSULFIDE DIBROMIDE AS VERSATILE REAGENTS FOR BETA-LACTAM SYNTHESIS
Cossio, Fernando P.,Ganboa, Inaki,Palomo, Claudio
, p. 3041 - 3044 (2007/10/02)
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.
Synthesis of β-lactams from acetic acids and imines induced by phenyl dichlorophosphate reagent
Arrieta,Cossio,Palomo
, p. 1703 - 1712 (2007/10/02)
The development of a practical method for the preparation of vinylamino-β-lactams from Dane salts and Schiff bases is described. Among the reagents known to produce β-lactams from imines and acetic acids, only phenyl dichlorophosphate and 1-methyl-2-chloropyridinium iodide are suitable for the synthesis of vinylamino-β-lactams. Reaction of acetic acids with ethanolimine derivatives promoted by phenyl dichlorophosphate affords oxazolidines instead of β-lactams. Protection of the hydroxyl group as the trimethylsilyl ether in the starting Schiff bases provides a convenient route to the corresponding β-lactams instead of oxazolidines. Some observations on the scope of the method are made.
