Structural influence on the anisotropic intermolecular hydrogen bonding in solid state of substituted thioureas: evidence by X-ray crystal structure

Venkatachalam, T. K.; Sudbeck, Elise A.; Uçkun, Fatih M.

doi:10.1016/j.molstruc.2003.08.022

Cited by 20 publications

(16 citation statements)

References 45 publications

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“…This implies that N3-H group participate in a strong intramolecular hydrogen bond interaction with the thiazole nitrogen of the type N3-H···N=C. 10,11,16 The other N1-H group is involved in an intermolecular hydrogen bond with either the thiocarbonyl of the thiourea of the type N1-H···S=C, [17][18][19][20] or the carbonyl of the amino acid residue of the type N1-H···O=C.…”

Section: Methodsmentioning

confidence: 99%

Syntheses and reactions of methyl [3-(4-phenyl-thiazol-2-yl)-thioureido] alkanoates and related compounds

Fathalla¹

2008

Arkivoc

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Section: Methodsmentioning

confidence: 99%

Syntheses and reactions of methyl [3-(4-phenyl-thiazol-2-yl)-thioureido] alkanoates and related compounds

Fathalla¹

2008

Arkivoc

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“…[5][6][7] The reaction of methyl 2-[3-(2-phenylquinazolin-4-yl)thioureido]acetate (5a) with absolute ethanol in the presence of potassium hydroxide furnished the transesterification product 5f (Scheme 2). With methyl iodide, 5a underwent chemoselective S-alkylation to form isothiourea 6…”

Section: Methodsmentioning

confidence: 99%

“…Several heterocyclic thioureas have been reported as a new class of potent non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase (NNRTIs) such phenethylthiazolyl-thiourea (PETT) derivatives. Uckun et al [5][6][7] described the synthesis of a number of heterocyclic thioureas having an amino acid ester or aryl side chain as NNRTIs.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and reactions of methyl 2-[3-(2-phenylquinazolin-4-yl)thioureido]alkanoates

Fathalla¹,

Pazdera²

2007

Arkivoc

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“…We might conclude that an intramolecular hydrogen bond interaction of the type N-H···N=C participates in the stabilization of this structure and the consequent formation of a single tautomer [13][14][15]20]. The 13 C NMR spectrum of compound 4 reveals carbon signals at δ 178.20, 158.79, 155.75, and 47.14 ppm assigned to C=S, C-2, C-4, and CH 3 , respectively.…”

mentioning

confidence: 94%

Synthesis of new 1-substituted 4-(2-phenylquinazolin-4-yl)-and 4-(2-phenylquinazolin-4-ylidene) thiosemicarbazides

Fathalla

Pazdera

2008

Chem Heterocycl Comp

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Keywords: quinazoline, thiosemicarbazide, domino reaction, hydrogen bond interaction.Finding a new methodologies for the synthesis of a family of biologically potent compounds by employing building blocks with multifunctional groups is a key target for drug development. Thioureas and thiosemicarbazides appear to be ideal candidates for the development of such processes since they are the core structural fragments in the families of compounds known to display biological activities, e.g. pyrazole [1], 1,2,4-triazoles [1-5], 1,3,4-oxadiazoles [3, 4], 1,3,4-thiadiazoles [1, 4, 5], 1,3-thiazoles [6], 1,2,4-triazepine [7], 1,3,4-thiadiazine [8], 1,3,4-thiadiazepine [9, 10], etc. The reported synthetic routes for thioureas and thiosemicarbazides were usually addition of amines and hydrazines to isothiocyanates [11]. Recently we described the domino syntheses of 3,3-disubstituted 1-(2-phenyl-3H-quinazolin-4-ylidene)-thioureas [12] and 3-N-substituted 1-N-(2-phenylquinazolin-4-yl)thioureas [13-15] by a simple reaction of the in situ generated N-(2-cyanophenyl)benzimidoyl isothiocyanate with secondary and primary amines, respectively.Herein we report an efficient synthesis of 1-substituted 4-(2-phenyl-quinazolin-4-yl)-and 4-(2-phenylquinazolin-4-ylidene) thiosemicarbazides by a simple reaction of N-(2-cyanophenyl)benzimidoyl isothiocyanate (1) with hydrazines. Thus, the reactions of imidoyl isothiocyanate 1 with 1,1-dimethyl-hydrazine (2), 1,1-diphenylhydrazine (3), or hydrazine hydrate in acetone gave three different interesting products: 1,1-dimethyl-4-(2-phenylquinazolin-4-yl) thiosemicarbazide (4), 1,1-diphenyl-4-(2-phenylquinazolin-4(3H)-ylidene) thiosemicarbazide (5), or 4-(2-phenylquinazolin-4(3H)-ylidene)-2-(propen-2-yl)-1-(propan-2-ylidene) thiosemicarbazide (6), respectively (Scheme 1).

show abstract

Structural influence on the anisotropic intermolecular hydrogen bonding in solid state of substituted thioureas: evidence by X-ray crystal structure

Cited by 20 publications

References 45 publications

Syntheses and reactions of methyl [3-(4-phenyl-thiazol-2-yl)-thioureido] alkanoates and related compounds

Syntheses and reactions of methyl [3-(4-phenyl-thiazol-2-yl)-thioureido] alkanoates and related compounds

Synthesis and reactions of methyl 2-[3-(2-phenylquinazolin-4-yl)thioureido]alkanoates

Synthesis of new 1-substituted 4-(2-phenylquinazolin-4-yl)-and 4-(2-phenylquinazolin-4-ylidene) thiosemicarbazides

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