Synthesis and crystal structure of N(12)-(2-hydroxy-2-phenylethyl)cytisine

Shishkin, D. V.; Baibulatova, N. Z.; Лобов, А. Н.; Ivanov, S. P.; Спирихин, Л. В.; Докичев, В. А.

doi:10.1007/s10600-010-9525-5

Cited by 4 publications

(1 citation statement)

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“…Various studies report modern methods for the synthesis of cytisine (Bara ´t et al, 2018;Hirschha ¨user et al, 2011;O'Neill et al, 2000;Pe ´rez et al, 2012) or cytisine modification (Brel, 2016;Kulakov et al, 2010;Kulakov & Nurkenov, 2012;Shishkin et al, 2010;Marrie `re et al, 2000;Frasinyuk et al, 2007). From the large number of cytisine derivatives, substances with biological activity (Tutka et al, 2019;Gotti & Clementi, 2021;Liu et al, 2020) and agents used in medicine (Tabex) have been found.…”

Section: Chemical Contextmentioning

confidence: 99%

Syntheses, crystal structures and Hirshfeld surface analyses of N-arylsulfonyl derivatives of cytisine

et al. 2023

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By arylsulfonylation of cytisine in the presence of triethylamine, three new compounds have been obtained in good yields: (7R,9R)-N-[(4-ethylphenyl)sulfonyl]cytisine, C19H22N2O3S (I) {systematic name: (1R,5R)-3-[(4-ethylphenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one}, (7R,9R)-N-[(4-chlorophenyl)sulfonyl]cytisine, C17H17ClN2O3S (II) {systematic name: (1R,5R)-3-[(4-chlorophenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one} and (7R,9R)-N-[(3-nitrophenyl)sulfonyl]cytisine, C17H17N3O5S (III) {systematic name: (1R,5R)-3-[(3-nitrophenyl)sulfonyl]-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one}. The crystal structures of the compounds were determined on the basis of single-crystal X-ray diffraction data. The crystal structures of (I)–(III) are distinguished by the arrangement of two fragments of the molecule around the sulfonyl site. For all structures, weak C—H...O hydrogen bonds are developed. Hirshfeld surface analysis shows that H...H (for I and II) and H...O/O...H (for III) interactions make the most important contribution to the crystal packing.

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