51535-00-3Relevant academic research and scientific papers
Condensed 2-pyrrolidinone-1,2-oxazines from lithium enolate of 1-benzyl-5-oxo-3-pyrrolidinecarboxylic acid and β-aryl, β-nitroenamines
Felluga, Fulvia,Gombac, Valentina,Pitacco, Giuliana,Valentin, Ennio,Zangrando, Ennio,Morganti, Stefano,Rizzato, Egon,Spinelli, Domenico,Petrillo, Giovanni
, p. 8787 - 8791 (2006)
The reaction of the lithium enolate of 1-benzyl-5-oxo-3-pyrrolidinecarboxylic acid 3 with a series of β-aryl, β-nitroenamines unexpectedly afforded 6-aryl-2-benzyl-4-oxa-1-oxo-3a-methoxycarbonyl-2,5-diazaindenes 9a-d, whose structure was determined by analytical and NMR spectroscopical analysis. The structure of 9b was further confirmed by X-ray analysis. A reasonable mechanism for their formation is given.
Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines
Chardon, Aurélien,Mohy El Dine, Tharwat,Legay, Rémi,De Paolis, Micha?l,Rouden, Jacques,Blanchet, Jér?me
supporting information, p. 2005 - 2009 (2017/02/19)
A reduction of various aryl, alkyl, and α,β-unsaturated amides with phenylsilane, catalysed by a borinic acid, is reported. The unprecedented reaction was carried out under very mild conditions and led to useful amines. Furthermore, the reaction tolerates a variety of functional groups. Initial investigations implicated that an intermediate diarylhydroborane is involved in the reaction mechanism.
A method for preparing west Naira Tanzania
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Paragraph 0030; 0031; 0032; 0033, (2017/08/25)
The invention discloses a preparation method for nebracetam, and belongs to the technical field of medical chemistry. The key points of the technical scheme of the invention are as follows: the preparation method for the nebracetam comprises the following steps: performing Michael addition reaction and intramolecular cyclization on dimethyl itaconate and benzylamine serving as raw materials to obtain 1-benzyl-5-oxopyrrolidin-3-carboxylic methyl ester; reducing the 1-benzyl-5-oxopyrrolidin-3-carboxylic methyl ester by sodium borohydride to obtain 1-benzyl-4-hydroxymethyl-pyrrolidine-2-keton; performing methyl sulfonylation on the 1-benzyl-4-hydroxymethyl-pyrrolidine-2-keton to obtain 1-benzyl-5-oxopyrrolidin-3-carboxylic methanesulfonate; finally, performing ammonification and reduction on the 1-benzyl-5-oxopyrrolidin-3-carboxylic methanesulfonate by using ammonia water to obtain the nebracetam. The preparation method is simple in preparation process, easy to control and high in target product yield, and meets the requirement for green chemistry.
Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions
Mateo, Pierre,Cinqualbre, Joséphine E.,Meyer Mojzes, Melinda,Schenk, Kurt,Renaud, Philippe
supporting information, p. 12318 - 12327 (2017/12/08)
A simple procedure for the conversion of tertiary lactams to 2-monoalkylated cyclic amines is described. The reaction sequence involves conversion of a lactam to a thioiminium ion followed by reaction with an organocopper (RCu) reagent and final reduction with triacetoxyborohydride. The reaction is high yielding and shows an excellent functional group tolerance. Its utility is demonstrated by a rapid synthesis of indolizidine 167B. The excellent chemoselectivity of the process, where only monoalkylation products are formed, is rationalized by a mechanism involving the formation of a transient enamine.
Inhibition of noroviruses by piperazine derivatives
Dou, Dengfeng,He, Guijia,Mandadapu, Sivakoteswara Rao,Aravapalli, Sridhar,Kim, Yunjeong,Chang, Kyeong-Ok,Groutas, William C.
supporting information; experimental part, p. 377 - 379 (2012/02/16)
There is currently an unmet need for the development of small-molecule therapeutics for norovirus infection. The piperazine scaffold, a privileged structure embodied in many pharmacological agents, was used to synthesize an array of structurally-diverse derivatives which were screened for anti-norovius activity in a cell-based replicon system. The studies described herein demonstrate for the first time that functionalized piperazine derivatives possess anti-norovirus activity. Furthermore, these studies have led to the identification of two promising compounds (6a and 9l) that can be used as a launching pad for the optimization of potency, cytotoxicity, and drug-like characteristics.
Concise synthesis of bicyclic aminals by way of catalytic intramolecular C-H amination and evaluation of their reactivity as iminium precursors
Rodriguez-Lucena, David,Morin, Marie S.T.,Compain, Philippe
scheme or table, p. 155 - 162 (2012/04/04)
The concise synthesis of fused bicyclic aminals by way of intramolecular rhodium-catalyzed C-H amination is reported as well as the evaluation of their reactivity as iminium precursors. In contrast to the well-studied N,O-acetal systems, the aminals synthesized were found to be particularly stable under reaction conditions used for nucleophilic addition.
Synthesis of new β-trifluoromethyl containing GABA and β-fluoromethyl containing N-benzylpyrrolidinones
Gerus, Igor I.,Mironets, Roman V.,Shaitanova, Elena N.,Kukhar, Valery P.
experimental part, p. 224 - 228 (2010/04/30)
A whole series of 3-(mono-, di-, trifluoro)methyl-substituted N-benzylpyrrolidinones 5a-c was synthesized by deoxyfluorination of corresponding 3-functionalized N-benzylpyrrolidinones. New β-trifluoromethyl containing GABA 4a was obtained in two alternative ways: by successive hydrolysis and hydrogenolysis of 3-trifluoromethyl N-benzylpyrrolidinone 5a and from trifluoroacetone as starting compound.
Intramolecular 1,6-addition to 2-pyridones. Mechanism and synthetic scope
Gallagher, Timothy,Derrick, Ian,Durkin, Patrick M.,Haseler, Claire A.,Hirschhaeuser, Christoph,Magrone, Pietro
supporting information; experimental part, p. 3766 - 3774 (2010/08/20)
Figure presented The scope and limitations of the intramolecular 1,6-addition of an enolate to a 2-pyridone moiety, a reaction that has found application in the synthesis of the lupin alkaloids, have been probed. This nucleophilic addition process has been shown to be reversible and favored in the case of (less stabilized) amide and lactam enolates, which readily form five- and six-membered bi-/tricyclic products. Alternative enolates (ketone, ester, thiolactam) and a variety of different acceptors (isoquinolinone, pyrimidinone, pyrazinone, pyridopyrazinone) have been evaluated, and a range of competing side reactions have been identified and characterized using various techniques, including in situ IR.
Discovery of an orally efficaceous 4-phenoxypyrrolidine-based BACE-1 inhibitor
Iserloh,Pan,Stamford,Kennedy,Zhang,Zhang,Parker,McHugh,Favreau,Strickland,Voigt
, p. 418 - 422 (2008/09/18)
Based on a lead compound identified from the patent literature, we developed patentably novel BACE-1 inhibitors by introducing a cyclic amine scaffold as embodied by 1a and 1b. Extensive SAR studies assessed a variety of isophthalamide replacements including substituted pyrrolidinones and ultimately led to the identification of 11. Due to its favorable overall profile, 11 has been extensively profiled in various in vivo settings.
Synthesis of functionalized nitrogen heterocycles by radical decarboxylation of β- and γ-amino acids
Boto, Alicia,Hernandez, Rosendo,De Leon, Yolanda,Murguia, Jose R.,Rodriguez-Afonso, Abigail
, p. 673 - 682 (2007/10/03)
Iodinated or oxygenated nitrogen heterocycles are obtained by radical decarboxylation of β- and γ-amino acids. This mild, versatile reaction is applied to the synthesis of bioactive products, such as 4-arylpiperidines, hydroxylated piperidines, and new antifungal agents.
