Syntheses and crystal structures of two N-substituted thio-imidazoles

Williamson, Craig; Storey, John M. D.; Harrison, William T. A.

doi:10.1007/s10870-005-9032-x

Cited by 12 publications

(5 citation statements)

References 6 publications

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“…Imidazoline-2-thiones were also synthesized by cyclization of linear precursor molecules [4 -6]. The thione function was most conveniently introduced by reaction of heterocyclic quaternary salts with sulfur in MeOH/K 2 CO 3 [7 -9], or MeOH/pyridine/DBU [10,11]. Recently, the use of CH 2 Cl 2 /Et 3 N [12] and THF/KOtBu [13] was reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Crystal Structures of New 1,3-Disubstituted Imidazoline-2-thiones

Laus

Kahlenberg

Wurst

et al. 2013

Zeitschrift Für Naturforschung B

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Two methods (MeOH/K 2 CO 3 , pyridine/Et 3 N) were assessed for the introduction of sulfur into the 2-position of 1,3-disubstituted quaternary imidazolium salts 1-9 (Cl, I, BF 4 , PF 6 , CH 3 OSO 3 were used as anions) to yield nine 1,3-disubstituted imidazoline-2-thiones 10-18 (1, 10: R 1 = CH 3 , R 2 = CH 3 ; 2, 11: R 1 = OCH 2 Ph, R 2 = CH 3 ; 3, 12: R 1 = OCH 3 , R 2 = CH 3 ; 4, 13: R 1 = OCH 3 , R 2 = OCH 3 ; 5, 14: R 1 = NH 2 , R 2 = CH 2 Ph; 6, 15: R 1 = NCHPh, R 2 = CH 3 ; 7, 16: R 1 = NH 2 , R 2 = CH 3 ; 8, 17: R 1 = NCHPh, R 2 = NCHPh; 9, 18: R 1 = NH 2 , R 2 = OCH 3 ). Compounds 11-18 represent N-alkyloxy and N-amino imidazoline-2-thiones, whereas 10 served as reference compound. The first method was advantageous for the conversion 1 → 10 due to faster reaction, whereas in the reaction 2 → 11 considerable amounts of by-products were formed. Pure thiones 11, 14, 16, 17, and 18 were obtained only by the second method. Both methods worked for the synthesis of the methoxy derivatives 12 and 13 from 3 and 4, and the benzylideneamino derivative 15 from 6. 1-Amino-3-methylimidazoline-2-thione (16) was also prepared by hydrolysis of the benzylideneamino derivative 15. Crystal structures of seven 1,3-disubstituted imidazoline-2-thiones were determined by singlecrystal X-ray diffraction. Intermolecular C-H···S contacts were identified and, additionally, N-H···S interactions in aminothiones 14 and 16. The 1 H NMR shifts of 10 and 13 were satisfactorily correlated with the Kamlet-Abboud-Taft π * and β parameters in ten solvents. From the lack of correlation with the α parameter and from the C=S bond length (average 1.68Å) a significant contribution of a mesoionic imidazolium-2-thiolate resonance structure seems unlikely.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Crystal Structures of New 1,3-Disubstituted Imidazoline-2-thiones

Laus

Kahlenberg

Wurst

et al. 2013

Zeitschrift Für Naturforschung B

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“…The molecular structure has not a planar conformation. Imidazole rings A (N1/N2/C1-C3), B (N3/N4/C4-C6) and C correlated with the contribution of resonance structures involving the lone pair electrons of the adjacent N atoms [18]. In the crystal, the cations, anions and uncoordinated water molecules are linked by intermolecular O H···O hydrogen bonds and weak intermolecular O H···S and C H···S interaction, generating a three-dimensional network (Fig.…”

Section: Resultsmentioning

confidence: 99%

Hexaaquamanganese(II) bis[hydrotris(3-methyl-2-thioxo-1-imidazolyl) borate] Tetrahydrate: A Non-coordinating Borate Ligand with Manganese(II) Metal Ion

Jayakumar¹,

Mohideen²,

Rahiman³

2015

Molecular Crystals and Liquid Crystals

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The metallation of a tripodal ligand, hydrotris(3-methyl-2-thioxo-1-imidazolyl)borate with manganese(II) salt gave an unusual title compound, [Mn(H 2 O) 6 ] (C 12 H 16 N 6 BS 3 ) 2 .4H 2 O. The presence of soft donor atom in the borate moiety may be the cause of non-coordinating interaction with metal ion. The manganese(II) ion is coordinated with six water molecules leads to distorted octahedral geometry. In the crystal, the cations, anions and uncoordinated water molecules are linked by intermolecular O H···O hydrogen bonds and week intermolecular O H···S and C H···S interaction,generating a three-dimensional network. The thermal behavior of the title compound was also investigated.

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“…Ansell et al demonstrated that [MMIm]I can readily react with elemental St oy ield 1,3-dimethylimidazole-2-thione in the presence of K 2 CO 3 in methanol. [94] This "MeOH/K 2 CO 3 " method has since been utilized to prepare av ariety of chalcogenones,i ncluding 1,3-dialkylimidazole-2-thione/ selone, [95,96] bridged bis(imidazoline-2-thione/selone), [97][98][99] and bridged mixed bidentate N-heterocyclic carbene (NHC)/sulfur ligands, [100] starting from the corresponding imidazolium salts and chalcogens.O ther "base/solvent" systems such as MeOH/pyridine/DBU, [101] pyridine/Et 3 N, [102] and THF/KO(t-Bu) [103] have also been investigated for the synthesis of imidazole-2-chalcogenones by the reaction of quaternary imidazolium salts with chalcogens.…”

Section: Reactions Of Chalcogen-containing Ionic Liquidsmentioning

confidence: 99%

Inorganic Synthesis Based on Reactions of Ionic Liquids and Deep Eutectic Solvents

et al. 2021

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Michael Ruck received his PhD from the University of Stuttgart in 1991 with Prof. Arndt Simon. After his habilitation at the University of Karlsruhe in 1997, he was aHeisenberg fellow of the German Science Foundation. Since 2000 he has been Full Professor of InorganicC hemistry at the Technische UniversitätD resden, where he has served as Dean of the Faculty of Science and Vice Rector.Hehas repeatedly been appointed aF ellow of the Max Planck Society and awarded the Steinhofer Research Award and the Will Kleber Commemorative Coin. His research interestsi nclude solid-state chemistry and sustainable material syntheses.

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Syntheses and crystal structures of two N-substituted thio-imidazoles

Cited by 12 publications

References 6 publications

Synthesis and Crystal Structures of New 1,3-Disubstituted Imidazoline-2-thiones

Synthesis and Crystal Structures of New 1,3-Disubstituted Imidazoline-2-thiones

Hexaaquamanganese(II) bis[hydrotris(3-methyl-2-thioxo-1-imidazolyl) borate] Tetrahydrate: A Non-coordinating Borate Ligand with Manganese(II) Metal Ion

Inorganic Synthesis Based on Reactions of Ionic Liquids and Deep Eutectic Solvents

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