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A versatile synthesis of benzothieno-annelated 1,2-dihydropyridine and 1,2,3,4-tetrahydropyridine derivatives: the effect of the structure of benzothieno-annelated pyridinium salts on their reduction by sodium borohydride

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Abstract

Benzothieno[2,3-c]pyridinium and benzothieno[2,3-c]quinolinium salts were synthesized either by quaternization of benzothieno[2,3-c]pyridines, or recyclization of benzothieno[2,3-c]pyrylium salts with primary amines. One-pot synthesis of benzothieno[3,2-g]indolizinium salts from 1-(3-chloropropyl)-benzothieno[2,3-c]pyrylium included consequent recyclization of the pyrylium core by ammonia into a pyridine intermediate and its further intramolecular quaternization reaction. Depending on the structure of benzothieno-annelated pyridinium salts, their reaction with sodium borohydride in methanol results in reduction of the pyridine core into tetrahydropyridine or dihydropyridine derivatives. Whereas reduction of benzothieno[2,3-c]pyridinium and benzothieno[3,2-g]indolizinium salts readily yields benzothieno-annelated tetrahydropyridines as a complex mixture of stereoisomers, reduction of benzothieno[2,3-c]quinolinium salts results in dihydropyridine derivatives. The structure of the latter, in particular, was confirmed by single-crystal X-ray diffraction analysis.

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Authors and Affiliations

  1. L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, 70 R. Luxemburg str., 83114, Donetsk, Ukraine

    Maksym A. Kryuchkov, Igor F. Perepichka & Sergei V. Tolkunov

  2. Institute for Scintillation Materials, National Academy of Sciences of Ukraine, 60 Lenina ave., 61001, Kharkiv, Ukraine

    Roman I. Zubatyuk & Oleg V. Shishkin

Authors
  1. Maksym A. Kryuchkov
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  2. Roman I. Zubatyuk
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  3. Igor F. Perepichka
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  4. Oleg V. Shishkin
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  5. Sergei V. Tolkunov
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Correspondence to Maksym A. Kryuchkov.

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Kryuchkov, M.A., Zubatyuk, R.I., Perepichka, I.F. et al. A versatile synthesis of benzothieno-annelated 1,2-dihydropyridine and 1,2,3,4-tetrahydropyridine derivatives: the effect of the structure of benzothieno-annelated pyridinium salts on their reduction by sodium borohydride. Monatsh Chem 141, 35–43 (2010). https://doi.org/10.1007/s00706-009-0222-7

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  • DOI: https://doi.org/10.1007/s00706-009-0222-7

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