A synthetic route to a novel type of conformationally constrained N-aryloxazolidinones

[Display omitted] The synthesis of N-aryloxazolidinone 1, a conformationally constrained analog of linezolid embodying a tricyclic pyrrolo[1,2-a][4,1]benzoxazepine moiety as the N-aryl substituent, is reported. The synthetic route involves the successive construction of the pyrrole, oxazepine, and o...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2005-05, Vol.15 (10), p.2515-2517
Main Authors: Griera, Rosa, Cantos-Llopart, Carme, Amat, Mercedes, Bosch, Joan, del Castillo, Juan-C., Huguet, Joan
Format: Article
Language:English
Subjects:
Antibiotics
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Chemistry
Constrained analogs
Exact sciences and technology
General aspects
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Linezolid
Medical sciences
Molecular Conformation
N-Aryloxazolidinones
Organic chemistry
Oxazolidinones - chemical synthesis
Oxazolidinones - chemistry
Oxazolidinones - pharmacology
Pharmacology. Drug treatments
Preparations and properties
Pyrrolo[1,2-a][4,1]benzoxazepine
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Summary:[Display omitted] The synthesis of N-aryloxazolidinone 1, a conformationally constrained analog of linezolid embodying a tricyclic pyrrolo[1,2-a][4,1]benzoxazepine moiety as the N-aryl substituent, is reported. The synthetic route involves the successive construction of the pyrrole, oxazepine, and oxazolidinone rings, with incorporation of the isoxazolylamino moiety in the last synthetic steps.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2005.03.071