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Keywords = β-aryl-γ-lactams

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15 pages, 4236 KiB  
Article
Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs
by Attila Márió Remete and Loránd Kiss
Molecules 2019, 24(1), 161; https://doi.org/10.3390/molecules24010161 - 3 Jan 2019
Cited by 5 | Viewed by 3947
Abstract
Stereocontrolled synthesis of some amino acid-based carbocyclic nucleoside analogs containing ring C=C bond has been performed on β- and γ-lactam basis. Key steps were N-arylation of readily available β- or γ-lactam-derived amino ester isomers and amino alcohols with 5-amino-4,6-dichloropyrimidine; ring closure of [...] Read more.
Stereocontrolled synthesis of some amino acid-based carbocyclic nucleoside analogs containing ring C=C bond has been performed on β- and γ-lactam basis. Key steps were N-arylation of readily available β- or γ-lactam-derived amino ester isomers and amino alcohols with 5-amino-4,6-dichloropyrimidine; ring closure of the formed adduct with HC(OMe)3 and nucleophilic displacement of chlorine with various N-nucleophiles in the resulting 6-chloropurine moiety. Full article
(This article belongs to the Special Issue Small Molecule Drug Design)
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16 pages, 1986 KiB  
Article
Efficient Synthesis of β-Aryl-γ-lactams and Their Resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen
by Iris J. Montoya-Balbás, Berenice Valentín-Guevara, Estefanía López-Mendoza, Irma Linzaga-Elizalde, Mario Ordoñez and Perla Román-Bravo
Molecules 2015, 20(12), 22028-22043; https://doi.org/10.3390/molecules201219830 - 10 Dec 2015
Cited by 18 | Viewed by 10469
Abstract
An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the [...] Read more.
An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the reduction of the γ-nitroester in the presence of Raney nickel and the subsequent saponification/decarboxylation reaction. The utility of this methodology was highlighted by the preparation of enantiomerically-pure (R)- and (S)-Baclofen hydrochloride. Full article
(This article belongs to the Section Organic Chemistry)
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