Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement: A theoretical and experimental studies

V. M. Boitsov, N. A. Knyazev, S. V. Shmakov, S. Y.U. Vyazmin, D. M. Nikolaev, O. B. Chakchir, A. V. Stepakov

Research output: Contribution to journalArticlepeer-review

Abstract

Benzo[h]isoquinoline scaffold is of interest as a rigid subunit that can be useful for constructing biologically active products. However, no good-yielded synthetic pathway to this ring system has been reported yet. Herein, a facile one-pot synthesis from N-aryl itaconimides and 1,3-diarylisobenzofuran via strong acid triggered skeletal rearrangement reaction is described. Theoretical study for this rearrangement is provided at M11/cc-pVDZ level of theory. Antitumor activity of obtained benzo[h]isoquinoline derivatives against human erythroleukemia K562 cell line was evaluated in vitro by MTS-assay.

Original languageEnglish
Pages (from-to)2133-2138
Number of pages6
JournalAsian Journal of Chemistry
Volume31
Issue number9
DOIs
StatePublished - 2019

Scopus subject areas

  • Chemistry(all)

Keywords

  • 1
  • 3-Diarylisobenzofuran
  • Acid induced rearrangement
  • Antitumor activity
  • Benzo[h]isoquinoline
  • N-Aryl Itaconimides

Fingerprint

Dive into the research topics of 'Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement: A theoretical and experimental studies'. Together they form a unique fingerprint.

Cite this