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Title: 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

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, C{sub 11}H{sub 12}N{sub 2}O (1a); 2-[2-(4-chlorophenyl)-2-oxoethoxy]-6,7,8,9-tetrahydro-5H-cyclohepta[b] pyridine-3-carbonitrile, C{sub 19}H{sub 17}ClN{sub 2}O{sub 2} (2a); (3-amino-6,7,8,9-tetrahydro-5H-cyclohepta[b]furo[3,2-e]pyridin-2-yl)(4- chlorophenyl)methanone, C{sub 19}H{sub 17}ClN{sub 2}O{sub 2} (3); 2-oxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carboxamide, C{sub 12}H{sub 16}N{sub 2}O{sub 2} (4); 2-[2-(4-chorophenyl)-2-oxoethoxy]-5,6,7,8,9,10 -hexahydrocycloocta[b]pyridine-3-carboxamide, C{sub 20}H{sub 21}ClN{sub 2}O{sub 3} (5a); 1-[2-(4-chlorophenyl)-2-oxoethyl]-2-oxo-1,2,5,6,7,8,9,10 -octahydrocycloocta[b]pyridine-3-carboxamide, C{sub 20}H{sub 21}ClN{sub 2}O{sub 3} (5b); and 2-[2-(4-chlorophenyl)-2-oxoethoxy]-5,6,7,8,9,10-hexahydrocycloocta[b] pyridine-3-carbonitrile, C{sub 20}H{sub 19}ClN{sub 2}O{sub 2}, (6). All compounds are characterized by {sup 1}H NMR spectroscopy, and their crystal structures are determined by X-ray diffraction.

Authors:
;  [1];  [2]
  1. Moscow State University, Faculty of Chemistry (Russian Federation)
  2. National Academy of Sciences of Armenia, Mnjoyan Institute of Fine Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry (Armenia)
Publication Date:
OSTI Identifier:
22645202
Resource Type:
Journal Article
Resource Relation:
Journal Name: Crystallography Reports; Journal Volume: 62; Journal Issue: 2; Other Information: Copyright (c) 2017 Pleiades Publishing, Inc.; Country of input: International Atomic Energy Agency (IAEA)
Country of Publication:
United States
Language:
English
Subject:
75 CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND SUPERFLUIDITY; CRYSTAL STRUCTURE; HEPTANE; NUCLEAR MAGNETIC RESONANCE; OCTANE; PYRIDINE; SPECTROSCOPY; X-RAY DIFFRACTION

Citation Formats

Rybakov, V. B., E-mail: Rybakov20021@yandex.ru, Babaev, E. V., and Paronikyan, E. G., E-mail: Ervand.paronikyan@mail.ru. 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. United States: N. p., 2017. Web. doi:10.1134/S1063774517020249.
Rybakov, V. B., E-mail: Rybakov20021@yandex.ru, Babaev, E. V., & Paronikyan, E. G., E-mail: Ervand.paronikyan@mail.ru. 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. United States. doi:10.1134/S1063774517020249.
Rybakov, V. B., E-mail: Rybakov20021@yandex.ru, Babaev, E. V., and Paronikyan, E. G., E-mail: Ervand.paronikyan@mail.ru. Wed . "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". United States. doi:10.1134/S1063774517020249.
@article{osti_22645202,
title = {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},
author = {Rybakov, V. B., E-mail: Rybakov20021@yandex.ru and Babaev, E. V. and Paronikyan, E. G., E-mail: Ervand.paronikyan@mail.ru},
abstractNote = {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, C{sub 11}H{sub 12}N{sub 2}O (1a); 2-[2-(4-chlorophenyl)-2-oxoethoxy]-6,7,8,9-tetrahydro-5H-cyclohepta[b] pyridine-3-carbonitrile, C{sub 19}H{sub 17}ClN{sub 2}O{sub 2} (2a); (3-amino-6,7,8,9-tetrahydro-5H-cyclohepta[b]furo[3,2-e]pyridin-2-yl)(4- chlorophenyl)methanone, C{sub 19}H{sub 17}ClN{sub 2}O{sub 2} (3); 2-oxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carboxamide, C{sub 12}H{sub 16}N{sub 2}O{sub 2} (4); 2-[2-(4-chorophenyl)-2-oxoethoxy]-5,6,7,8,9,10 -hexahydrocycloocta[b]pyridine-3-carboxamide, C{sub 20}H{sub 21}ClN{sub 2}O{sub 3} (5a); 1-[2-(4-chlorophenyl)-2-oxoethyl]-2-oxo-1,2,5,6,7,8,9,10 -octahydrocycloocta[b]pyridine-3-carboxamide, C{sub 20}H{sub 21}ClN{sub 2}O{sub 3} (5b); and 2-[2-(4-chlorophenyl)-2-oxoethoxy]-5,6,7,8,9,10-hexahydrocycloocta[b] pyridine-3-carbonitrile, C{sub 20}H{sub 19}ClN{sub 2}O{sub 2}, (6). All compounds are characterized by {sup 1}H NMR spectroscopy, and their crystal structures are determined by X-ray diffraction.},
doi = {10.1134/S1063774517020249},
journal = {Crystallography Reports},
number = 2,
volume = 62,
place = {United States},
year = {Wed Mar 15 00:00:00 EDT 2017},
month = {Wed Mar 15 00:00:00 EDT 2017}
}
  • The structures of four compounds are studied using single-crystal X-ray diffraction: 1-[2-(4-chlorophenyl)-2-oxoethyl]-2-oxo-1,2,5,6,7,8-hexahydroquinoline -3-carbonitrile [a = 4.908(4) A, b = 11.644(10) A, c = 13.587(2) A, {beta} = 94.31(5) deg., Z = 2, space group P2{sub 1}]; 2-[2-(4-chlorophenyl)-2-oxoethoxy]-5,6,7,8-tetrahydroquinoline -3-carbonitrile [a = 7.6142(8) A, b = 14.778(2) A, c = 14.132(2) A, {beta} = 100.38(1) deg., Z = 4, space group P2{sub 1}/c]; 4-(aminocarbonyl)-2-(chlorophenyl)-6,7,8,9-tetrahydro[1.3]oxazolo[3,2-a] quinolin-3-ium perchlorate [a = 5.589(7) A, b = 24.724(15) A, c = 13.727(5) A, {beta} = 97.66(9) deg., Z = 4, space group P2{sub 1}/n]; and (3-amino-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-2-yl)-(4-chlorophenyl) methanone [a = 7.150(2) A, b = 7.4288(10) A, c =more » 15.314(3) A, {alpha} = 98.030(10) deg., {beta} = 99.21(2) deg., {gamma} = 105.34(2) deg., Z = 2, space group P1-bar]. The structures are solved by direct methods and refined by the full-matrix least-squares procedure in the anisotropic approximation to R = 0.0728, 0.0439, 0.1228, and 0.0541, respectively. The structure of 1-(4-chlorophenyl)-4-piperidin-1-yl-8,9-dihydro-7H-pyrrolo[3.2.1-ij] quinoline-5-carboxamide [a = 23.9895(9) A, b = 5.1557(3) A, c = 17.0959(9) A, {beta} = 106.43 deg., Z = 4, space group P{sub 1}/c] is investigated by X-ray powder diffraction. This structure is solved using the grid search procedure and refined by the Rietveld method to R{sub wp} = 0.0773, R{sub exp} = 0.0540, R{sub p} = 0.0585, R{sub b} = 0.1107, and {chi}{sup 2} = 1.78.« less
  • Ring closure of the bis-Grignard derived from cis-1,3-bis(bromomethyl)cyclopentane (5) on R{sub 2}GeCl{sub 2} (R = Ph or Me) afforded the 3-germabicyclo(3.2.1)octane system 6 or 7. Bromine cleavage of a phenyl group in 3,3-diphenyl-3-germabicyclo(3.2.1)octane (6) and subsequent nucleophilic displacement of the bromide allowed differing substitution on the germanium atom. Crystals of 6 were grown from 95% ethanol and found to crystallize in the orthorhombic space group P{sub na2}C{sub A}2{nu} (No. 33, variation) with Z = 4, a = 7.921 (2) {angstrom}, b = 31.565 (5) {angstrom}, c = 6.530 (2) {angstrom}. The physical and spectral properties of these new molecules aremore » presented.« less
  • The compound [UO{sub 2}(NO{sub 3}){sub 2}(H{sub 2}O){sub 2}] {center_dot} 2C{sub 12}H{sub 18}O was synthesized and studied by IR spectroscopy and X-ray diffraction. The structure consists of the neutral island groups [UO{sub 2}(NO{sub 3}){sub 2}(H{sub 2}O){sub 2}], which belong to the crystal-chemical group AB{sup 01}{sub 2}M{sup 1}{sub 2} (A = UO{sub 2}{sup 2+}, B{sup 01} = NO{sub 3}{sup -}, M{sup 1} = H{sub 2}O) of uranyl complexes, and 1-adamantyl methyl ketone molecules. The characteristic features of the association of the complexes [UO{sub 2}(NO{sub 3}){sub 2}(H{sub 2}O){sub 2}] and 1-adamantyl methyl ketone molecules in the crystal structure via hydrogen bonds are consideredmore » with the use of Voronoi-Dirichlet polyhedra.« less
  • The structures of 2,8-dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-2,3,4,4a,5, 9b-hexahydro1H-pyrido[4,3-b]indole trihydrobromide (I) (a = 12.865(4) Angstrom-Sign , b = 14.281(3) Angstrom-Sign , c = 13.553(3) Angstrom-Sign , Z = 4, sp. gr. Pna2{sub 1}) and 2,8-dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido [4,3-b]indole dihydrobromide (II) (a = 13.9704(14) Angstrom-Sign , b = 14.4447(15) Angstrom-Sign , c = 10.7819(12) Angstrom-Sign , {beta} = 107.58(1) Degree-Sign , Z = 4, sp. gr. P2{sub 1}/c) were studied by single-crystal X-ray diffraction. The structures were solved by direct methods and refined by the full-matrix least-squares method with anisotropic displacement parameters to the R factors of 0.0603 and 0.0446, respectively. All Br{sup -} anions form hydrogenmore » bonds with protonated nitrogen atoms. The synthesis and physicochemical parameters of these two compounds are reported.« less