Skeletally Diverse Synthesis of Innovative [2,1-c]-1,4-Oxazepine and [1,4]-Quinoxaline Systems

Chia Hsin Lee, Wen Chun Wu, Prasad S. Dangate, Li Ching Shen, Wen-Sheng Chung*, Chung-Ming Sun

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

An efficient, innovative synthesis of [2,1-c]-1, 4-oxazepine and [1,4]-quinoxaline heterocycles along with the embodied pyrimido-pyrrolo motifs was established. Initially, the pyrrole ring was installed using microwave irradiation through an intramolecular base-catalyzed cyclization between acetyl bromomethyl pyrimidine dione and o-amino phenyl methanol or o-phenylenediamine methyl benzoates. Furthermore, oxazepine, and quinoxaline scaffolds were constructed by an acid-catalyzed condensation with a variety of aldehydes by an unconventional Pictet-Spengler reaction strategy. An important aspect of this work is to build novel heterocyclic ring systems with potential medicinal interest.

Original languageEnglish
Pages (from-to)623-630
Number of pages8
JournalACS Combinatorial Science
Volume17
Issue number10
DOIs
StatePublished - 12 Oct 2015

Keywords

  • oxazepine
  • pyrimido-pyrrolo motifs
  • quinoxaline
  • unconventional Pictet-Spengler reaction strategy

Fingerprint Dive into the research topics of 'Skeletally Diverse Synthesis of Innovative [2,1-c]-1,4-Oxazepine and [1,4]-Quinoxaline Systems'. Together they form a unique fingerprint.

Cite this