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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

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… Click to show full 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.

Keywords: chlorophenyl; pyridine carbonitrile; pyridine; ray diffraction

Journal Title: Crystallography Reports
Year Published: 2017

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