A highly efficient synthetic route to a new 1,4-diazepene skeleton, 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepine, was established where Knoevenagel condensation of readily available two fragments, N-substituted pyrrole-2-carboxaldehyde and α-azidoketone, followed by intramolecular aza-Wittig reaction under Staudinger azide reduction conditions permitted facile access to a poly-substituted 1,4-diazepine ring system for the first time. Successful application of this protocol to construct new 1-alkoxy-3-acylisoquinolines and 1-alkoxy-3-acyl-β-carbolines is also demonstrated. This journal is
Bibliographical noteFunding Information:
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718, NRF-2020R1A2C2005961, and NRF-2020R1I1A1A01074930) for generous financial support.
© The Royal Society of Chemistry.
All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry