Expansion of diazepine heterocyclic chemical space: via sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5 H -pyrrolo[1,2- d] [1,4]diazepines

Anuradha Dagar, Ikyon Kim

Research output: Contribution to journalArticlepeer-review

Abstract

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

Original languageEnglish
Pages (from-to)9836-9851
Number of pages16
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number48
DOIs
Publication statusPublished - 2020 Dec 28

Bibliographical note

Funding Information:
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718, NRF-2020R1A2C2005961, and NRF-2020R1I1A1A01074930) for generous financial support.

Publisher Copyright:
© The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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