Cascade Cyclization/Annulation of β-Enamino Diketones and <i>o</i>-Phenylenediamine: A Strategy to Access Pyrrole-fused 1,5-Benzodiazepines
Herein, we introduce an unprecedented cascade reaction for the assembly of pyrrole-fused 1,5-benzodiazepine frameworks. These diverse privileged scaffolds were controllably constructed by intramolecular cyclization of β-enamino diketone, followed by annulation with <i>o</i>-phenylenediamine. The protocol features efficient one-pot cascade cyclization/annulation, performed under simple and mild reaction conditions. The products are obtained in a metal-free manner, in good to excellent yields (65-91%), and represent a fused heterocyclic scaffold that is not yet found in nature.
Authors
- Hélio G. Bonacorso (ORCID: https://orcid.org/0000-0002-2745-2061)
- Julia Poletto (ORCID: https://orcid.org/0000-0001-6752-4552)
- Jeniffer Nascimento Ascencio Camargo
- Fernanda A. Rosa (ORCID: https://orcid.org/0000-0003-0027-7117)
- Julia C. M. Willig
- Michael J. V. da Silva (ORCID: https://orcid.org/0009-0006-0116-237X)
Institutions
- Universidade Estadual de Maringá (BR)
- Universidade Tecnológica Federal do Paraná (BR)
- Universidade Federal de Santa Maria (BR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-11-13
- DOI
- https://doi.org/10.1021/acs.joc.4c02483
- Primary Topic
- Synthesis and pharmacology of benzodiazepine derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação Araucária