Thiourea and Selenourea and Their Applications

Koketsu, Mamoru; Ishihara, Hideharu

doi:10.2174/157017906778699521

Cited by 45 publications

(16 citation statements)

References 111 publications

(113 reference statements)

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“…For a general background to the biological activity of thiourea, see: Koketsu & Ishihara (2006). For heterocyclic derivatives, metal complexes and molecular electronics, see: Zeng et al (2003) Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

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3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea

et al. 2012

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The title compound, C10H8N4O2S, was synthesized from furoyl isothiocynate and 2-aminopyrimidine in dry acetone. The two N—H groups are in an anti conformation with respect to each other and one N—H group is anti to the C=S group while the other is syn. The amide C=S and the C=O groups are syn to each other. The mean plane of the central thiourea fragment forms dihedral angles of 13.50 (14) and 5.03 (11)° with the furan and pyrimidine rings, respectively. The dihedral angle between the furan and pyrimidine rings is 18.43 (10)°. The molecular conformation is stabilized by an intramolecular N—H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, molecules are linked by pairs of N—H⋯N and weak C—H⋯S hydrogen bonds to form inversion dimers.

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Section: Related Literaturementioning

confidence: 99%

“…Butcher Comment Thiourea and its derivatives are known to exhibit a wide variety of biological activities (Koketsu & Ishihara, 2006). These are also widely used as precursors or intermediates towards the syntheisis of a variety of heterocyclic compounds (Zeng et al, 2003;D'hooghe, et al, 2005).…”

Section: -[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thioureamentioning

confidence: 99%

3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea

et al. 2012

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“…Compounds of this class have not been previously structurally characterized, despite the fact that N , N ′-disubstituted thioureas have varied applications. 20,21 Some examples of these applications include their use (i) as antibacterial, 22,23,24 antifungal, 24,25 antiviral, 26,27,28 anti-HIV, 28 antimalarial, 23 antituberculous, 28,29 antihistamine, 30 and anticancer 27 agents, (ii) in organocatalysis, 31,32,33 and (iii) in crystal engineering. 34,35 …”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural characterization of 1-arylimidazole-2-thiones and N,N′-aryldiethoxyethylthioureas with electronically diverse substituents: a manifold of hydrogen bonding networks

Palmer

Parkin

2014

New J. Chem.

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The 1-arylimidazole-2-thiones, (HmimAr) [Ar = 3,4,5-C6H2(OMe)3, 2,4-C6H3(NO2)(OMe), 2,4,6-C6H2Cl3 and 3,5-C6H3(CF3)2], which feature electronically diverse substituents, may be obtained via acid-catalyzed ring closure of the corresponding N,N′-aryldiethoxyethylthiourea derivatives, ArN(H)C(S)N(H)CH2CH(OEt)2, (H2detuAr), which in turn are obtained via treatment of aminoacetaldehyde diethyl acetal, H2NCH2CH(OEt)2, with the respective arylisothiocyanates (ArNCS). The molecular structures of all of the above N,N′-aryldiethoxyethylthioureas and 1-arylimidazole-2-thiones have been determined by X-ray diffraction, thereby demonstrating that the substituents have a profound effect on the crystal structures. For example, each of the N,N′-aryldiethoxyethylthiourea derivatives adopts a different hydrogen bonding pattern. Specifically, the hydrogen-bonding network in (i) H2detuArCl3 consists of chains of 9-membered rings, with an [ R22(9)] motif, that feature one N–H ⋯ O and one N–H ⋯ S interaction, (ii) H2detuArOMe,NO2 consists of chains of 6-membered rings, with an [ R21(6)] motif, that feature two head-to-tail N–H ⋯ S interactions, (iii) H2detuAr(CF3)2 consists of a dimer that features two pairs of N–H ⋯ O interactions, of which each pair is a component of an 8-membered ring with an [ R22(8)] motif, and (iv) H2detuAr(OMe)3 consists of a chain of head-to-head dimeric rings with a basic [ R22(16)] motif, a notable feature of which is that sulfur does not play a role as a hydrogen bond acceptor. Each of the 1-arylimidazole-2-thiones exists as a “head-to-head” hydrogen-bonded dimer in the solid state, with an [ R22(8)] motif. However, while the hydrogen-bonded motifs for HmimArCl3 and HmimAr(OMe)3 are planar, those for HmimAr(CF3)2 and HmimArOMe,NO2 are extremely puckered, with fold angles of 24.2° (mean value) and 45.7°, respectively.

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“…After 5 h, sodium chloroacetate (0.23 g, 2.0 mmol) was added and the reaction mixture was stirred overnight. 137.55, 134.03, 132.72, 131.68, 126.45, 48.67, 41.96, 20.24;IR (KBr) ν: 3335, 2985, 2971, 2093, 1594, 1520, 1350, 1158, 1040 64, 147.78, 139.60, 134.82, 131.32, 129.01, 124.14, 49.68, 42.06;IR (KBr) ν: 3399, 1515, 1474, 1366, 1172, 1126, 1086, 1033 41, 131.42, 131.37, 125.57, 123.89, 113.87, 110.63, 41.44;IR (KBr) ν: 3096, 3019, 2923, 1619, 1510, 1450, 1414, 1364, 1296, 1262, 1171, 1046 3036,2962,2920,1591,1505,1450,1382,1292,1260,1197,1152,1085,1040,746,727,692,663,583 (d,J＝8.4 Hz,2H),7.45 (d,J＝8.4 Hz,2H),2H),1H), 2.39 (s, 3H); 13 C NMR (DMSO-d 6 , 100 MHz) δ: 169. …”

Section: Instrumentsmentioning

confidence: 99%

Facile Synthesis of N‐Sulfonylcyclothioureas in Water

Wan

et al. 2011

Chin. J. Chem.

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A sequential one-pot synthesis of N-sulfonylcyclothioureas from N-monosulfonyl diamines, CS 2 and chloroacetic acid at room temperature in water is described. In the absence of highly toxic thiophosgene and organic solvents, this method is environmentally benign. Simple reaction conditions, easy purification of the products, good yields and thioglycolic acid as the useful byproduct are also important attributes of this methodology. The plausible mechanism including tandem reactions is proposed.

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Thiourea and Selenourea and Their Applications

Abstract: This review provides a comprehensive survey of the recent progress in the various preparative methods and the application as catalyst of the thiourea and selenourea, their application in the preparation of heterocycles and their biological significances.

Cited by 45 publications

References 111 publications

3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea

3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea

Synthesis and structural characterization of 1-arylimidazole-2-thiones and N,N′-aryldiethoxyethylthioureas with electronically diverse substituents: a manifold of hydrogen bonding networks

Facile Synthesis of N‐Sulfonylcyclothioureas in Water

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