19340-71-7Relevant academic research and scientific papers
Synthesis of β-lactams and cyclo-β-dipeptides from β-amino acids: Experimental observations and theoretical analysis
Escalante, Jaime,González-Tototzin, Miguel A,Avi?a, Judit,Mu?oz-Mu?iz, Omar,Juaristi, Eusebio
, p. 1883 - 1890 (2001)
The cyclization of β-amino acids by means of activating agents is one of the most useful approaches for the construction of β-lactams; however, we found that when PhP(O)Cl2 (in Et3N) is employed as the activating agent, cyclization o
Highly stereoselective intramolecular Buchner reaction of diazoacetamides catalyzed by a Ru(ii)-Pheox complex
Phan Thi Thanh, Nga,Tone, Masaya,Inoue, Hayato,Fujisawa, Ikuhide,Iwasa, Seiji
, p. 13398 - 13401 (2019/11/14)
This work reports the first efficient enantioselective intramolecular Buchner reaction of diazoacetamides. The Ru(ii)-Pheox catalyst was shown to be highly efficient in this transformation in terms of both the regio-and enantioselectivity (up to 99% ee) giving the desired products in quantitative yield.
Access to β-lactams by enantioselective palladium(0)-catalyzed C(sp3)-H alkylation
Pedroni, Julia,Boghi, Michele,Saget, Tanguy,Cramer, Nicolai
supporting information, p. 9064 - 9067 (2014/09/17)
β-Lactams are very important structural motifs because of their broad biological activities as well as their propensity to engage in ring-opening reactions. Transition-metal-catalyzed C-H functionalizations have emerged as strategy enabling yet uncommon h
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,
The acid-mediated ring opening/cyclisation reaction of N-benzyl-α- aryl-azetidinones
King, Frank D.,Caddick, Stephen
, p. 9350 - 9354 (2012/11/07)
N-Benzyl-4-aryl-azetidinones undergo ring opening with triflic acid to form N-benzyl-cinnamamides, which either undergo cyclisation to give 5-aryl-benzazepin-3-ones or N-debenzylation to give cinnamamides.
β-Lactam derivatives as enzyme inhibitors: Halogenated β-lactams and related compounds
Elriati, Ali,Loose, Jutta,Mayrhofer, Roswitha,Bergmann, Hans-Joachim,Otto, Hans-Hartwig
experimental part, p. 835 - 846 (2009/09/06)
Different modifications of the imine - acyl chloride reaction were used for the synthesis of 3-mono- and 3,3-dihalogenated 1,4-diaryl substituted β-lactams. Furthermore, these β-lactams were modified by halogen substitution either at the aryl at position
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.
Orthogonal N,N-deprotection strategies of β-amino esters
Bull, Steven D.,Davies, Stephen G.,Kelly, Peter M.,Gianotti, Massimo,Smith, Andrew D.
, p. 3106 - 3111 (2007/10/03)
β-Amino esters derived from the stereoselective conjugate addition of homochiral lithium N-benzyl-N-α-methyl-4-methoxybenzylamide to α,β-unsaturated esters may be orthogonally mono-N-deprotected under either oxidative or acid-promoted reaction conditions. Further oxidative deprotection affordsβ-amino acids or β-lactams.
