Synthesis and halocyclization of 2-alkenylthioquinolines

Kim, D. G.

doi:10.1007/s10593-009-0195-9

“…It is known that in a similar reaction, 2-(allylsulfanyl)quinoline forms 1-iodomethyl-1,2-dihydro[1,3]thiazolo[3,2-a]quinolinium polyiodides of various stoichiometric composition (Kim et al, 2015). This fact suggests that the formation of the bithiazoloquinolinium dication apparently proceeds according to a mechanism similar to the known halogencyclization reactions of S-allyl (Kim et al, 1996(Kim et al, , 2008(Kim et al, , 2015 and S-propargyl derivatives of thioquinolines.…”

Section: Introductionmentioning

confidence: 83%

Why are reactions of 2- and 8-thioquinoline derivatives with iodine different?

Rudakov

¹

,

Сташ

²

,

Makarov

³

et al. 2018

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The crystal structures of 1,2-dihydro-1,1'-bi[thiazolo[3,2-a]quinoline]-10a,10a'-diium diiodide hemihydrate, CHNS·2I·0.5HO, and 1,2-dihydro-1,1'-bi[thiazolo[3,2-a]quinoline]-10a,10a'-diium iodide triiodide, CHNS·I·I, obtained during the reaction of 1,4-bis(quinolin-2-ylsulfanyl)but-2-yne (2TQB) with iodine, have been determined at 120 K. The crystalline products contain the dication as a result of the reaction proceeding along the iodocyclization pathway. This is fundamentally different from the previously observed reaction of 1,4-bis(quinolin-8-ylsulfanyl)but-2-yne (8TQB) with iodine under similar conditions. A comparative analysis of the possible conformational states indicates differences in the relative stabilities and free rotation for the 2- and 8-thioquinoline derivatives which lead to a disparity in the convergence of the potential reaction centres for 2TQB and 8TQB.

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“…Yield 0.141 g (71%). 1 H NMR spectrum, , ppm (J, Hz): 3.15 (1H, t, 4 J = 2.6, CH≡); 4.19 (2H, d, 4 J = 2.6, SCH 2 ); 7.45 (1H, d, 3 …”

Section: -Propargylthioquinolinementioning

confidence: 99%

“…

Keywords: 1-bromomethylthiazolo[3,2-a]quinolinium bromide, propargyl bromide, 1-iodomethylthiazolo[3,2-a]quinolinium iodide, 2-mercaptoquinoline, 2-propargylthioquinoline.The synthesis of the thiazolo[3,2-a]quinolinium system is carried out by dehydration of -(2-quinolylthio) ketones [1] or -(quinolylthio)acetic acids [2], and the halocyclization of 2-vinylthioquinoline [3].We have shown that the reaction of 2-propargylthioquinoline (1) with bromine or iodine does not stop at the stage of formation of 1-halomethylidene-1,2-dihydrothiazolo[3,2-a]quinolinium halides 2a,b but further isomerizes to give the 1-halomethylthiazolo[3,2-a]quinolinium halides 3a,b. Compound 1 was prepared by the reaction of 2-mercaptoquinoline with propargyl bromide in the presence of sodium 2-propoxide in 2-propanol.

…”

mentioning

confidence: 99%

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Synthesis of the thiazolo[3,2-a]quinolinium system

Kim

¹

,

Вершинина

²

2010

Chem Heterocycl Comp

Self Cite

5

0

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Keywords: 1-bromomethylthiazolo[3,2-a]quinolinium bromide, propargyl bromide, 1-iodomethylthiazolo[3,2-a]quinolinium iodide, 2-mercaptoquinoline, 2-propargylthioquinoline.The synthesis of the thiazolo[3,2-a]quinolinium system is carried out by dehydration of -(2-quinolylthio) ketones [1] or -(quinolylthio)acetic acids [2], and the halocyclization of 2-vinylthioquinoline [3].We have shown that the reaction of 2-propargylthioquinoline (1) with bromine or iodine does not stop at the stage of formation of 1-halomethylidene-1,2-dihydrothiazolo[3,2-a]quinolinium halides 2a,b but further isomerizes to give the 1-halomethylthiazolo[3,2-a]quinolinium halides 3a,b. Compound 1 was prepared by the reaction of 2-mercaptoquinoline with propargyl bromide in the presence of sodium 2-propoxide in 2-propanol. N SH Br N S N H S N S X X X 2 N S X X 1 2n+1 3a,b 2n+1 2a,b 2-PrONa, 2-PrOH + + 2, 3 a X = I, n = 0; b X = Br, n = 1The 1 H NMR spectra for compounds 3a,b show signals for the protons of the CH 2 I (4.71) or CH 2 Br group (4.74 ppm) and for the H-2 proton at 8.09 and 8.04 ppm respectively.In contrast to compound 1 the 3-formyl-2-propargylthioquinoline reacts with the halogens to form 1-halomethylidene-2H-thiazolo[3,2-a]quinolinium halides [4].1 H NMR spectra were recorded on a Bruker DRX-400 spectrometer (400 MHz) using DMSO-d 6 and with TMS as internal standard. Mass spectra (EI, 70 eV) were taken on a Hewlett-Packard GC/MS instrument with an HP-5890 gas chromatograph.

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“…-The comparison of calculated wavelengths corresponding to the basic electronic transitions and experimental UV-Vis characteristics has been made under solvent change conditions. Experimental 2-Allylthioquinoline and 2-ethylthioquinoline compounds were synthesized according to [14,15] in order to investigate their spectral properties. Dichloromethane, carbon tetrachloride, benzene, acetone, ethanol (analytical grade) were used as solvents.…”

Section: Introductionmentioning

confidence: 99%

Combined approach to uv-vis study of 2-allyl and 2-ethylthioquinolines in various solutions

Ilkaeva²,

et al. 2016

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Combined approach to analysis of 2-allylthioquinoline and 2-ethylthioquinoline solutions has been performed on the basis of UV-Vis spectroscopy. Experimental and calculated electronic absorption spectra of these compounds in various solvents: acetone, benzene, carbon tetrachloride, dichloromethane, ethanol have been considered. The negative solvatochromic effect has been observed. The results of our calculations have revealed that the spectra of various conformers of 2-allylthioquinoline differ more essentially than the spectra of 2ethylthioquinoline conformers. It has been shown that the location of λ max band doesn't drastically depend on allyl or alkyl substitution at the sulfur atom.

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Synthesis and halocyclization of 2-alkenylthioquinolines

Cited by 10 publications

References 2 publications

Why are reactions of 2- and 8-thioquinoline derivatives with iodine different?

Why are reactions of 2- and 8-thioquinoline derivatives with iodine different?

Synthesis of the thiazolo[3,2-a]quinolinium system

Combined approach to uv-vis study of 2-allyl and 2-ethylthioquinolines in various solutions

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