One-Pot Quinazolin-4-ylidenethiourea Synthesis via N-(2-Cyanophenyl)benzimidoyl isothiocyanate

Fathalla, Walid; Čajan, Michal; Marek, Jaromı́r; Pazdera, Pavel

doi:10.3390/60700574

Cited by 20 publications

(36 citation statements)

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“…20 However a strong query still remains that is the development of simple, mild and efficient methods for preparation of quinazoline derivatives linked to amino acid residues by a spacer and the evaluation of their biological activities. In view of these facts and in continuation of our efforts in studing the chemoselective reactions of heterocyclic amides [21][22][23] and thioamides, 20,[24][25][26][27][28][29][30][31][32][33][34][35][36][37] we found interesting to synthesize a series of quinazoline derivatives linked to amino acids by a spacer. Here in we wish to report a novel synthesis of 3-arylquinazoline-2,4-dione and use this precursor in the synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Ismail¹,

Ali²,

Fathalla³

et al. 2017

Arkivoc

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A series of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate 10-13a-f has been developed on the basis of the N-chemoselective reaction of 3-substituted quinazoline-2,4-diones 3a-d with ethyl chloroacetate and azide coupling method with amino acid ester hydrochloride. The precursor quinazoline diones 3a-d chemoselective reactions were studied using DFT(B3LYP)/6-311G level of theory and were prepared by a new rearrangement method from the corresponding 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-2-ylthio) acetohydrazide 6.

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Section: Introductionmentioning

confidence: 99%

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Ismail¹,

Ali²,

Fathalla³

et al. 2017

Arkivoc

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“…The sophistic approach to the synthesis of all three thiosemicarbazides 4, 5, and 6 is shown in Scheme 2 [12][13][14][15]. The reaction between hydrazine and acetone to form dimethylketazine (N,N'-diisopropylidenehydrazine) is well known [16,17].…”

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confidence: 99%

“…The structure assignment of thiosemicarbazides 4-6 is based on elemental analysis, 1 H, 13 C NMR spectral data, and on the correlation with fully analyzed references for N-(2-phenylquinazolin-4(3H)-ylidene)pyrrolidine-1-carbothioamide [12] and 1-benzyl-3-(2-phenylquinazolin-4-yl)thiourea [13] 13 C NMR spectral data of N-(2-phenylquinazolin-4(3H)-ylidene)pyrrolidine-1-carbothioamide [12] and 1-benzyl-3-(2-phenylquinazolin-4-yl)thiourea [13].…”

mentioning

confidence: 99%

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).

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“…This solution was stirred at 5 °C for 30 min, filtered and subsequently added in portions to a previously prepared solution of imidoyl isothiocyanate 1 (1.32 g, 5 mmol) in acetonitrile (30 mL). 8,9 The reaction mixture was stirred at room temperature for 24 h. The solvent was evaporated under reduced pressure, and the residue was crystallized from ethanol. …”

Section: Methyl 2-[3-(2-phenylquinazolin-4-yl)thioureido]alkanoates (mentioning

confidence: 99%

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

Fathalla¹,

Pazdera²

2007

Arkivoc

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One-Pot Quinazolin-4-ylidenethiourea Synthesis via N-(2-Cyanophenyl)benzimidoyl isothiocyanate

Cited by 20 publications

References 11 publications

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

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

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

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