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Cycloisomerization – a straightforward way to benzo[h]quinolines and benzo[c]acridines

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Chemistry of Heterocyclic Compounds Aims and scope

Cycloisomerization of 3-alkynyl-2-arylpyridines and quinolines offers a straightforward approach to benzo[h]quinolines and benzo[c]-acridines. Substituent at the triple bond governs a choice between transition metal or Brønsted acid catalysis. A direct electrophilic activation by trifluoromethanesulfonic acid induces an almost quantitative cyclization of the o-aryl(phenylethynyl) fragment. PtCl2 efficiently catalyzes cyclization of 2-aryl-3-ethynylhetarenes.

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This research was supported by the Ministry of Education and Science of the Russian Federation (grant of the President of the Russian Federation no. MK-5965.2016.3).

NMR and HRMS analyses were performed at the Saint Petersburg State University Center for Magnetic Resonance Resource and Center for Chemical Analysis and Materials Research.

The authors thank Dr. Alexey Fedorov (ETH Zurich) for his help in the preparation of this manuscript.

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Authors and Affiliations

  1. Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Ave., Saint Petersburg, 198504, Russia

    Aleksandr N. Shestakov, Alena S. Pankova & Mikhail A. Kuznetsov

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  1. Aleksandr N. Shestakov
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  2. Alena S. Pankova
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  3. Mikhail A. Kuznetsov
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Correspondence to Mikhail A. Kuznetsov.

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The Supplementary information file containing optimization of the Sonogashira reaction between pyridine 2a and TMS-acetylene and copies of 1H and 13C{1H} NMR spectra of all compounds is available from the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1103–1113

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Shestakov, A.N., Pankova, A.S. & Kuznetsov, M.A. Cycloisomerization – a straightforward way to benzo[h]quinolines and benzo[c]acridines. Chem Heterocycl Comp 53, 1103–1113 (2017). https://doi.org/10.1007/s10593-017-2179-5

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