Synthesis and steric structure of [2-(3-pyridyl)piperidino](2-vinyloxyethylamino)methanethione

Ibraev, M. K.; Турдыбеков, Д. М.; Takibaeva, A. T.; Нуркенов, О. А.; Турдыбеков, К. М.; Газалиев, А. М.; Адекенов, С. М.

doi:10.1134/s1070363206040232

Cited by 3 publications

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“…Somewhat unexpectedly, the pyridine substituent, attached at C7, was found in a pseudo-axial orientation. Such orientation of the pyridine substituent has also been reported for the crystals of thiourea derivatives of anabasine [37,38], where it has been ascribed to the presence of bulky substituents at the thiourea nitrogen. Moreover, the axial orientation of a methyl substituent has been observed in (1 0 R,6S)-1-(2 0 -hydroxy-1 0 -phenyl-ethyl)-6-methyl-piperidin-2-thione [39].…”

Section: X-ray Resultsmentioning

confidence: 76%

Thioanalogues of N-1-methylanabasine and nicotine – Synthesis and structure

Wojciechowska-Nowak

Boczoń

Warżajtis

et al. 2011

Journal of Molecular Structure

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Section: X-ray Resultsmentioning

confidence: 76%

Thioanalogues of N-1-methylanabasine and nicotine – Synthesis and structure

Wojciechowska-Nowak

Boczoń

Warżajtis

et al. 2011

Journal of Molecular Structure

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Synthesis, Spatial Structure, and Nootropic Activity of N-Cyanomethylanabasine

et al. 2022

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Synthesis of N-{2-[1-(prop-2-yn-1-yloxy)ethoxy]ethyl}-cytisinecarbothioamide and steric structure of its hydrolysis product, N-(2-hydroxyethyl)cytisinecarbothioamide

et al. 2010

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The reaction of 2-[1-(prop-2-yn-1-yloxy)ethoxy]ethyl isothiocyanate with alkaloid cytisine gave the corresponding thiourea derivative which was subjected to partial hydrolysis on heating in boiling aqueous ethanol or complete hydrolysis in the presence of a catalytic amount of an acid. The structure of the hydrolysis product, N-(2-hydroxyethyl)cytisinecarbothioamide, was proved by X-ray analysis.Thiourea derivatives constitute an important group of sulfur-containing organic compounds that are widely used in organic synthesis, as well as in industry, agriculture, and medicine. Most thiourea derivatives exhibit pharmacological activity, in particular antituberculous, antitumor, anti-inflammatory, antimicrobial, antiulcer, and other kinds of activity [1,2]. Thiourea derivatives are generally synthesized by reaction of isothiocyanates with amines. Reactions of various isothiocyanates with such alkaloids as cytisine and anabasine and ephedrine derivatives were studied previously [3][4][5]. Among the series of isothiocyanates, of specific interest is 2-vinyloxyethyl isothiocyanate which is a highly reactive difunctional synthon possessing unique synthetic potential, including the potentials of vinyl ethers and isothiocyanates. 2-[1-(Prop-2-yn-1-yloxy)ethoxy]ethyl isothiocyanate (I) was synthesized by electrophilic addition of prop-2-yn-1-ol at the double C=C bond of 2-vinyloxyethyl isothiocyanate in the presence of trifluoroacetic acid as catalyst according to the procedure reported in [6]. Acetal I opens wide prospects in the synthesis of more complex thiourea derivatives which undoubtedly attract interest from the viewpoint of design of new biologically active compounds.On the basis of isothiocyanate I and physiologically active alkaloid cytisine we synthesized N-{2-[1-(prop-2-yn-1-yloxy)ethoxy]ethyl}cytisinecarbothioamide (II) (Scheme 1). The reaction followed the generally

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Synthesis and steric structure of [2-(3-pyridyl)piperidino](2-vinyloxyethylamino)methanethione

Cited by 3 publications

References 1 publication

Thioanalogues of N-1-methylanabasine and nicotine – Synthesis and structure

Thioanalogues of N-1-methylanabasine and nicotine – Synthesis and structure

Synthesis, Spatial Structure, and Nootropic Activity of N-Cyanomethylanabasine

Synthesis of N-{2-[1-(prop-2-yn-1-yloxy)ethoxy]ethyl}-cytisinecarbothioamide and steric structure of its hydrolysis product, N-(2-hydroxyethyl)cytisinecarbothioamide

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