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Vol. 31 No. 9 (2019): Vol 31 Issue 9

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Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement: A Theoretical and Experimental Studies

https://doi.org/10.14233/ajchem.2019.22074
V.M. Boitsov
Saint-Petersburg Academic University, St. Petersburg 194021, Russia; Pavlov First Saint Petersburg State Medical University, St. Petersburg 197022, Russia
N.A. Knyazev
Saint-Petersburg Academic University, St. Petersburg 194021, Russia; Institute of Cytology of the Russian Academy of Science, St. Petersburg 194064, Russia
S.V. Shmakov
Saint-Petersburg Academic University, St. Petersburg 194021, Russia
S.Yu. Vyazmin
Saint-Petersburg Academic University, St. Petersburg 194021, Russia
D.M. Nikolaev
Saint-Petersburg Academic University, St. Petersburg 194021, Russia
O.B. Chakchir
Saint-Petersburg Academic University, St. Petersburg 194021, Russia
A.V. Stepakov
Chemistry Department, Saint-Petersburg State University, St. Petersburg 198504, Russia; Saint-Petersburg State Institute of Technology, St. Petersburg 190013, Russia

Corresponding Author(s) : V.M. Boitsov

bovitali@yandex.ru

Asian Journal of Chemistry, Vol. 31 No. 9 (2019): Vol 31 Issue 9

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.

Keywords

Benzo[h]isoquinoline N-Aryl Itaconimides 1,3-Diarylisobenzofuran Acid induced rearrangement Antitumor activity
Boitsov, V., Knyazev, N., Shmakov, S., Vyazmin, S., Nikolaev, D., Chakchir, O., & Stepakov, A. (2019). Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement: A Theoretical and Experimental Studies. Asian Journal of Chemistry, 31(9), 2133–2138. https://doi.org/10.14233/ajchem.2019.22074
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