Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement: A Theoretical and Experimental Studies-Reference-Cited by-同舟云学术

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

Published:2019-07-31 Issue:9 Volume:31 Page:2133-2138
ISSN:0975-427X
Container-title:Asian Journal of Chemistry
language:en
Short-container-title:Asian J. Chem.

Author:

Boitsov V.M.¹,Knyazev N.A.²,Shmakov S.V.¹,Vyazmin S.Yu.¹,Nikolaev D.M.¹,Chakchir O.B.¹,Stepakov A.V.³

Affiliation:

1. Saint-Petersburg Academic University, St. Petersburg 194021, Russia

2. Institute of Cytology of the Russian Academy of Science, St. Petersburg 194064, Russia

3. Chemistry Department, Saint-Petersburg State University, St. Petersburg 198504, Russia

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.

Publisher

Asian Journal of Chemistry

Subject

General Chemistry

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