4391-83-7Relevant academic research and scientific papers
NEW METHODS FOR β-LACTAM FORMATION FROM β-AMINO ACIDS WITH ORGANOPHOSPHOROUS COMPOUNDS
Kim, Chang Woo,Chung, Bong Young
, p. 2905 - 2906 (1990)
Ethyl dichlorophosphate, phenyl dichlorophosphate and phenylphosphonic dichloride are found to be very effective for β-lactam formation from β-amino acids.
Microwave-assisted synthesis of β-lactams and cyclo-β-dipeptides
Hernández-Vázquez, Luis G.,Leyva, Marco A.,Metta-Maga?a, Alejandro J.,Escalante, Jaime
, p. 2218 - 2230 (2013/02/22)
Different cyclo-β-dipeptides were prepared from corresponding N-substituted β-alanine derivatives under mild conditions using PhPOCl 2 as activating agent in benzene and Et3N as base. To evaluate β3-substituent influence,
Use of 2,2′-dibenzothiazolyl disulfide-triphenylphosphine and Lawesson's Reagent in the cyclization of β-amino acids
Kanwar, Seema,Sharma
, p. 1748 - 1752 (2007/10/03)
The disulfide reagents 2,2′-dithiobisbenzothiazole (MBTS) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's Reagent, LR) mediate the cyclization of β-amino acids with remarkable product yields. Compared to other cyclodehydrating agents, these have been found to be superior in terms of their cost, making them industrially viable. The advantageous properties of MBTS and LR make them useful and unique additions to the arsenal of cyclodehydrating agents.
(Chloromethylene)dimethylammonium chloride: A highly efficient reagent for the synthesis of β-lactams from β-amino acids
Kanwar, Seema,Sharma, Sain D.
, p. 705 - 707 (2007/10/03)
(Chloromethylene)dimethylammonium chloride 1, is a unique reagent that conveniently and efficiently mediates the amide bond formation in β-lactams via cyclodehydration of β-amino acids leading to β-lactam formation. The process involves the formation of a highly reactive activated ester of a β-amino acid which gets cyclised to the corresponding β-lactam in excellent yield. The reaction proceeds smoothly and cleanly as the by-products formed are the water soluble-dimethyl formamide and triethylamine hydrochloride.
Synthesis of monocyclic β-lactams via cyclodehydration of β-amino acids using POCl3
Sharma,Anand,Kaur, Gurpreet
, p. 1855 - 1862 (2007/10/03)
β-Lactams 2 have been synthesized through a convenient use of POCl3 via cyclodehydration of β-amino acids 1.
[Lewis acid]+[Co(CO)4]- complexes: A versatile class of catalysts for carbonylative ring expansion of epoxides and aziridines
Mahadevan, Viswanath,Getzler, Yutan D. Y. L.,Coates, Geoffrey W.
, p. 2781 - 2784 (2007/10/03)
Efficient carbonyl insertion into C-O and C-N bonds using [Lewis acid]+[Co(CO)4]- complexes 1 and 2 gives regio- and stereoselective carbonylation of a variety of epoxides and aziridines to yield β-lactones and β-lactams, respectively. Both transformations are proposed to occur by the same mechanism, yielding products with inversion of configuration at the site of CO insertion.
A facile synthesis of β-lactams by the cyclization of β-amino acids exploiting 3,3′-(phenylphosphoryl)-bis(1,3-thiazolidine-2-thione)
Nagao, Yoshimitsu,Kumagai, Toshio,Tamai, Satoshi,Matsunaga, Hiroshi,Abe, Takao,Inoue, Yoshinori
, p. 849 - 859 (2007/10/03)
3,3′-(Phenylphosphoryl)-bis(1,3-thiazolidine-2-thione) (5), obtained from phenylphosphonic dichloride (7) and sodium salt of 1,3-thiazolidine-2-thione (6), proved to be useful for intramolecular dehydration of various β-amino acids to give the correspondi
The Conversion of an Aziridine to a β-Lactam
Chamchaang, Wilaiporn,Pinhas, Allan R.
, p. 2943 - 2950 (2007/10/02)
A one-pot, inert atmosphere conversion of an aziridine to a β-lactam using nickel tetracarbonyl as the carbonyl source is described.In this reaction it is the less substituted carbon-nitrogen bond which is carbonylated.The proposed mechanism for this reac
