117106-15-7Relevant academic research and scientific papers
Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3)?H Carbamoylation
Dailler, David,Rocaboy, Ronan,Baudoin, Olivier
, p. 7218 - 7222 (2017/06/13)
A general and user-friendly synthesis of β-lactams is reported that makes use of Pd0-catalyzed carbamoylation of C(sp3)?H bonds, and operates under stoichiometric carbon monoxide in a two-chamber reactor. This reaction is compatible with a range of primary, secondary and activated tertiary C?H bonds, in contrast to previous methods based on C(sp3)?H activation. In addition, the feasibility of an enantioselective version using a chiral phosphonite ligand is demonstrated. Finally, this method can be employed to synthesize valuable enantiopure free β-lactams and β-amino acids.
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.
HIGHLY EFFICIENT OXAZOLONE-DERIVED REAGENTS FOR BETA-LACTAM FORMATION FROM BETA-AMINO ACIDS
Kunieda, Takehisa,Nagamatsu, Tomohisa,Higuchi, Tsunehiko,Hirobe, Masaaki
, p. 2203 - 2206 (2007/10/02)
Based on a unique leaving ability of 2-oxazolone moiety, highly efficient reagents have been developed for the formation of β-lactam compounds from β-amino acids including a facile preparation of penam, a basic skeleton of penicillins.
ARYL BIS (2-OXO-3-BENZOXAZOLINYL)PHOSPHINATE AND TRIS(2-OXO-3-BENZOXAZOLINYL)PHOSPHINE OXIDE: NEW CONDENSING REAGENTS FOR BETA-LACTAM FORMATION FROM BETA-AMINO ACIDS
Nagamatsu, Tomohisa,Kunieda, Takehisa
, p. 1249 - 1251 (2007/10/02)
Beta-lactam compounds including the penam, a basic skeleton of penicillins, are conveniently prepared by the dehydration of β-amino acids using new condensing reagents which are titled.Keywords - β-lactam; β-amino acid; penam; condensing reagent; 2-benzox
