Synthesis of novel p-nitrophenyl derivatives of thiazoline

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

doi:10.1134/s1070363206100343

Cited by 4 publications

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“…The reactions of various isothiocyanates with cytisine, anabasine, and ephedrine alkaloids have been previously studied [3][4][5]. 2-Vinyloxyethylisothiocyanate has attracted special interest as a starting material because it is a highly reactive bifunctional synthon with unique synthetic potential for simple vinyl ethers and isothiocyanates.…”

Section: And a M Gazalievmentioning

confidence: 99%

Synthesis and crystal structure of cytisino-N-(2-hydroxyethyl)-thiocarbamide

et al. 2009

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Section: And a M Gazalievmentioning

confidence: 99%

Synthesis and crystal structure of cytisino-N-(2-hydroxyethyl)-thiocarbamide

et al. 2009

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“…The piperidine ring adopted an ideal chair conformation (ΔC 8 [9], and anabasino(2-vinyloxyethylamino)methanethione [10]. The pyridine ring was planar within ±0.007 Å and was oriented axially (torsion angle C3C7C8C9 = 72.8°) relative to the piperidine ring, in contrast with anabasine O,O-diethylthiophosphate and anabasine O,O-diisopropylthiophosphate, where it was oriented equatorially.…”

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Synthesis of thiourea derivatives of the alkaloid anabasine and crystal structure of N-(anabasino1-thiocarbonyl)furan-2-carboxamide

Кулаков¹,

Нуркенов²,

Турдыбеков³

et al. 2009

Chem Nat Compd

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A series of new N-acylsubstituted thioureas, the compositions and structures of which were determined by IR and PMR spectroscopy and mass spectrometry, were synthesized from the alkaloid anabasine. The crystal structure of one of the products, N-(anabasino-1-thiocarbonyl)furan-2-carboxamide, was confirmed by x-ray structure analysis. It was also shown that this compound exhibited moderate antibacterial activity.Anabasine was discovered in 1929 by Orekhov A. P. from Anabasis aphilla and acts as a respiratory and cardiac stimulant. It is used in practical medicine as anabasine hydrochloride as an anti-smoking agent [1,2]. It was also broadly used previously as an insecticide for pests of such industrial cultures as cotton, fruit trees, and vegetables and gourds [3,4].Introducing a sulfur atom into physiologically active compounds not only decreases their overall toxicity due to the facile oxidizability of its derivatives in vivo but also produces other types of bioactivity. Also, it is known that most thiourea derivatives possess valuable pharmacological properties and are used as antituberculosis, antitumor, antimicrobial, anti-ulcer, and other therapeutic agents [5][6][7].We have previously synthesized thiourea derivatives of the alkaloids cytisine, 1-ephedrine, and d-pseudoephedrine with unsaturated and aromatic acyl derivatives.In continuation of that work we synthesized acyl-substituted thiourea derivatives based on anabasine by a convenient preparative isothiocyanate method. Isothiocyanates are very reactive compounds and react with amines under rather mild conditions.The starting isothiocyanates were synthesized by a convenient preparative in situ method (without isolation) by heating the corresponding acid chlorides (benzoylchloride, p-methylbenzoylchloride, p-bromobenzoylchloride, 2-furancarboxylic acid chloride) with KSCN in acetone. Further reaction of the resulting isothiocyanate lutions with anabasine under mild conditions formed 1-4.The products were white (or slightly yellowish) crystalline compounds that were soluble in polar organic solvents.

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“…The pyridine ring is planar within ±0.007 A° and is oriented axially (C3C7C8C9 torsion angle = -70.6°) relative to the piperidine ring, in contrast with anabasine O,O-diethylthiophosphate, where it is oriented equatorially. Such an orientation of the pyridine ring has been observed previously in N-anabasino(2-vinyloxyethylamino)methanethione [9] and N-(anabasino-1-carbonothioyl)furan-2-carboxamide [2]. In our opinion, such an orientation is due to non-bonded repulsion between the bulky substituent and the pyridine ring.…”

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confidence: 53%

“…The piperidine ring adopted an ideal chair conformation ('C s 8 = 0.7 A° ), like in anabasine O,O-diethylthiophosphate [8], N-anabasino(2-vinyloxyethylamino)methanethione [9], and N-(anabasino-1-carbonothioyl)furan-2-carboxamide [2]. The pyridine ring is planar within ±0.007 A° and is oriented axially (C3C7C8C9 torsion angle = -70.6°) relative to the piperidine ring, in contrast with anabasine O,O-diethylthiophosphate, where it is oriented equatorially.…”

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Synthesis and crystal structure of 5-methyl-2-(N-anabasinyl)-5,6-dihydro-1,3-thiazin-4-one from the alkaloid anabasine

Кулаков¹,

Турдыбеков²

2010

Chem Nat Compd

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UDC 547.94;one was synthesized in one step from the alkaloid anabasine. Its structure was proved by IR and PMR spectroscopy, mass spectrometry, and an x-ray structure analysis.Keywords: anabasine alkaloid, methacryloylisothiocyanate, intramolecular heterocyclization, 5,6-dihydro-1,3-thiazin-4-one, x-ray structure analysis.We have previously synthesized thiourea derivatives of the alkaloids cytisine, anabasine, d-pseudoephedrine, and l-ephedrine [1][2][3]. Many thiourea derivatives based on these alkaloids are excellent synthons for synthesizing new heterocyclic derivatives [4,5]. It was found [6] during preparation of the thiosemicarbazide derivative of isonicotinic acid that reaction of the corresponding hydrazide with methacryloylisothiocyanate produced its intramolecular heterocyclization product, 5,6-dihydro-1,3-thiazin-4-one.Therefore, we investigated the reaction of anabasine with methacryloylisothiocyanate (1), which was prepared in situ (without isolation) by heating methacryloylchloride with potassium thiocyanate in acetone. The reaction occurred with intramolecular heterocyclization of the intermediate methacrylamide derivative 2 into the corresponding product 3. The reaction occurred under rather mild conditions at 25-30°C in acetone.The yield and purity of the synthesized derivative 5,6-dihydro-1,3-thiazin-4-one (3) varied depending on the rate and order of addition of the reagents. The most acceptable (up to 40%) yields of 3 were obtained with slow dropping of a freshly prepared acetone solution of 1 to a vigorously stirred solution of anabasine.Only trace amounts of heterocyclization product 3 could be detected with the reverse order of addition of reagents to the reaction mixture. Its amount increased with time as a result of gradual spontaneous intramolecular cyclization of 2. The reaction mixture contained after work up also several unidentified crystalline and oily side products with -NH, -SCN, and C=O groups (IR spectroscopy data). As a result, it was impossible to separate and characterize in a pure state the methacrylamide intermediate 2.

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Synthesis of novel p-nitrophenyl derivatives of thiazoline

Cited by 4 publications

References 0 publications

Synthesis and crystal structure of cytisino-N-(2-hydroxyethyl)-thiocarbamide

Synthesis and crystal structure of cytisino-N-(2-hydroxyethyl)-thiocarbamide

Synthesis of thiourea derivatives of the alkaloid anabasine and crystal structure of N-(anabasino1-thiocarbonyl)furan-2-carboxamide

Synthesis and crystal structure of 5-methyl-2-(N-anabasinyl)-5,6-dihydro-1,3-thiazin-4-one from the alkaloid anabasine

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