Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement

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

In: Asian Journal of Chemistry, Vol. 31, No. 9, 2019, p. 2133-2138.

Research output: Contribution to journal › Article › peer-review

Author

Boitsov, V. M. ; Knyazev, N. A. ; Shmakov, S. V. ; Vyazmin, S. Y.U. ; Nikolaev, D. M. ; Chakchir, O. B. ; Stepakov, A. V. / Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement : A theoretical and experimental studies. In: Asian Journal of Chemistry. 2019 ; Vol. 31, No. 9. pp. 2133-2138.

BibTeX

@article{4bc675a7e6df4ead945f1cb9e00b0476,

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

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

author = "Boitsov, {V. M.} and Knyazev, {N. A.} and Shmakov, {S. V.} and Vyazmin, {S. Y.U.} and Nikolaev, {D. M.} and Chakchir, {O. B.} and Stepakov, {A. V.}",

note = "Funding Information: This work was financially supported by the Ministry of Education and Science of Russian Federation 16.9790.2017/ BCh. This research made use of resources from the X-ray Diffraction Centre, Computer Center, Centre for Magnetic Resonance, Educational Resource Center of Chemistry, Centre for Chemical Analysis and Materials of Saint-Petersburg State University and the equipment of the shared research facilities of HPC computing resources at Lomonosov Moscow State University. Publisher Copyright: {\textcopyright} 2019 Chemical Publishing Co.. All rights reserved. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",

year = "2019",

doi = "10.14233/ajchem.2019.22074",

language = "English",

volume = "31",

pages = "2133--2138",

journal = "Asian Journal of Chemistry",

issn = "0970-7077",

publisher = "Chemical Publishing Co.",

number = "9",

}

RIS

TY - JOUR

T1 - Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement

T2 - A theoretical and experimental studies

AU - Boitsov, V. M.

AU - Knyazev, N. A.

AU - Shmakov, S. V.

AU - Vyazmin, S. Y.U.

AU - Nikolaev, D. M.

AU - Chakchir, O. B.

AU - Stepakov, A. V.

N1 - Funding Information: This work was financially supported by the Ministry of Education and Science of Russian Federation 16.9790.2017/ BCh. This research made use of resources from the X-ray Diffraction Centre, Computer Center, Centre for Magnetic Resonance, Educational Resource Center of Chemistry, Centre for Chemical Analysis and Materials of Saint-Petersburg State University and the equipment of the shared research facilities of HPC computing resources at Lomonosov Moscow State University. Publisher Copyright: © 2019 Chemical Publishing Co.. All rights reserved. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

KW - 1

KW - 3-Diarylisobenzofuran

KW - Acid induced rearrangement

KW - Antitumor activity

KW - Benzo[h]isoquinoline

KW - N-Aryl Itaconimides

UR - http://www.scopus.com/inward/record.url?scp=85072993521&partnerID=8YFLogxK

U2 - 10.14233/ajchem.2019.22074

DO - 10.14233/ajchem.2019.22074

M3 - Article

AN - SCOPUS:85072993521

VL - 31

SP - 2133

EP - 2138

JO - Asian Journal of Chemistry

JF - Asian Journal of Chemistry

SN - 0970-7077

IS - 9

ER -

ID: 70822396