Synthesis of 1,4-Benzodiazepin-2-ones from Isatins
Various <i>N</i>-protected amino acids were coupled to isatin forming <i>N</i>-amino acylisatins. These novel <i>N</i>-acylisatins participate in a ring-opening reaction with either alcohols or amines to give the corresponding <i>N</i>-glyoxylesters or amides. Upon deprotection, cyclization under basic conditions produces 1,4-benzodiazepin-2-ones bearing ester or amide functionalities at the C5 position. This method provides an effective approach for the construction of benzodiazepine derivatives with diverse substituents at C3 and C5.
Authors
- Mohan Bhadbhade (ORCID: https://orcid.org/0000-0003-3693-9063)
- Yao Cheng (ORCID: https://orcid.org/0000-0001-5151-5651)
- David StC. Black (ORCID: https://orcid.org/0000-0001-9300-4737)
- Tsz Tin Yu (ORCID: https://orcid.org/0000-0002-8484-7342)
- Naresh Kumar (ORCID: https://orcid.org/0000-0002-0951-9621)
- Thanh Lê
Institutions
- UNSW Sydney (AU)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-23
- DOI
- https://doi.org/10.1021/acs.joc.5c00647
- Primary Topic
- Synthesis and pharmacology of benzodiazepine derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- University of New South Wales
- Australian Research Council