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Integrated Ugi-Based Assembly of Functionally, Skeletally, and Stereochemically Diverse 1,4-Benzodiazepin-2-ones

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† ‡ †Centro Singular de Investigación en Quı́mica Biológica y Materiales Moleculares (CIQUS) and ‡Departamento de Quı́mica Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain
§ Instituto de Sı́ntesis Orgánica, Facultad de Ciencias, Universidad de Alicante, E-03080 Alicante, Spain
∥ Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Universidad de Vigo, E-36310 Vigo, Spain
*E.S.: tel, ++34-881-815732; fax, ++34-981-528093; e-mail, [email protected]
Cite this: J. Org. Chem. 2015, 80, 3, 1533–1549
Publication Date (Web):January 5, 2015
https://doi.org/10.1021/jo502382q
Copyright © 2015 American Chemical Society
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    Abstract

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    A practical, integrated and versatile U-4CR-based assembly of 1,4-benzodiazepin-2-ones exhibiting functionally, skeletally, and stereochemically diverse substitution patterns is described. By virtue of its convergence, atom economy, and bond-forming efficiency, the methodology documented herein exemplifies the reconciliation of structural complexity and experimental simplicity in the context of medicinal chemistry projects.

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    Figures, a table, and CIF files giving NMR and HRMS spectra for described compounds, crystallographic structures, and chiral HPLC analysis of selected compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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