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X-ray mapping in heterocyclic design: 18. X-ray diffraction study of a series of derivatives of 3-cyanopyridine-2-one with annelated heptane and octane cycles

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Abstract

Seven new, previously unknown, bicyclic and tricyclic heterocycles based on derivatives of 3-cyanopyrid-2-ones are obtained: 2-oxo-2,5,6,7,8,9-hexahydro-1H-cyclohepta[b]pyridine-3-carbonitrile, C11H12N2O (1a); 2-[2-(4-chlorophenyl)-2-oxoethoxy]-6,7,8,9-tetrahydro-5Н-cyclohepta[b]pyridine-3-carbonitrile, C19H17ClN2O2 (2a); (3-amino-6,7,8,9-tetrahydro-5H-cyclohepta[b]furo[3,2-e]pyridin-2-yl)(4- chlorophenyl)methanone, C19H17ClN2O2 (3); 2-oxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carboxamide, C12H16N2O2 (4); 2-[2-(4-chorophenyl)-2-oxoethoxy]-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carboxamide, C20H21ClN2O3 (5a); 1-[2-(4-chlorophenyl)-2-oxoethyl]-2-oxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carboxamide, C20H21ClN2O3 (5b); and 2-[2-(4-chlorophenyl)-2-oxoethoxy]-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile, C20H19ClN2O2, (6). All compounds are characterized by 1H NMR spectroscopy, and their crystal structures are determined by X-ray diffraction.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Moscow, 119992, Russia

    V. B. Rybakov & E. V. Babaev

  2. Mnjoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, Yerevan, 375014, Armenia

    E. G. Paronikyan

Authors
  1. V. B. Rybakov
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  2. E. V. Babaev
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  3. E. G. Paronikyan
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Correspondence to V. B. Rybakov.

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Original Russian Text © V.B. Rybakov, E.V. Babaev, E.G. Paronikyan, 2017, published in Kristallografiya, 2017, Vol. 62, No. 2, pp. 218–230.

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Rybakov, V.B., Babaev, E.V. & Paronikyan, E.G. X-ray mapping in heterocyclic design: 18. X-ray diffraction study of a series of derivatives of 3-cyanopyridine-2-one with annelated heptane and octane cycles. Crystallogr. Rep. 62, 219–231 (2017). https://doi.org/10.1134/S1063774517020249

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  • DOI: https://doi.org/10.1134/S1063774517020249

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