Reaction Of Benzoyl Isothiocyanate Research Articles

Synthesis of new Fe(III), Co(II), and Cr(III) complexes of N‐(benzo[d]thiazol‐2‐ylcarbamothioyl)benzamide (H2L2): Structural characterization and biological activities

N‐(benzo[d]thiazol‐2‐ylcarbamothioyl)benzamide (H2L2) was synthesized as a novel thiosemicarbazide containing benzothiazole moiety, by the reaction of benzoyl isothiocyanate with 2‐aminobenzothiazole in benzene. The (H2L2) thiosemicarbazide and its isolated Cr(III), Fe(III), and Co(II) complexes were fully analyzed by different spectroscopic techniques. The thermal fragmentation of [Cr (HL2)Cl2(H2O)2].10H2O, [Co (HL2)Cl(H2O)2].6H2O, and [Fe(L2)Cl(H2O)2] were analyzed. We have also calculated the thermal parameters with using two different methods. The ligand undergoes tranamidation in the presence of PdCl2. Crystal structure of the product obtained by tranamidation is measured. Biological activities of those compounds were assessed as antioxidants, anticancer, and antimicrobial.

Novel Cr(III), Ni(II), and Zn(II) complexes of thiocarbamide derivative: Synthesis, investigation, theoretical, catalytic, potentiometric, molecular docking and biological studies

Throughout this research, the thiocarbamide derivative (H 2 L), and its Cr(III), Ni(II) and Zn(II) complexes have been reported. The thiocarbamide moiety was established with a reaction of benzoyl isothiocyanate and 1 H -1,2,4-triazol-3-amine. Structural elucidation of such compounds was achieved using elementary examination, spectral and magnetic experiments. The octahedral construction of the Cr(III) complex, the tetrahedral geometry of the Zn(III) complex and the mixed geometry (tetrahedral and square planar) of the Ni(II) complex have been verified by the optimization of structure using DFT. The action of Zn 2+ complex in the oxidative degradation of an organic azo-dye was investigated, and it showed promising results. The thermal degradation behavior of thiocarbamide metal complexes were studied as well as the calculation of the kinetic data for title compounds (E a , A, ΔH*, ΔS* and ΔG*) of thermal degradation steps has been tested utilizing two different techniques. Liver carcinoma (HePG2) and breast carcinoma (MCF-7) cytotoxicity as well as ABTS-antioxidant activities demonstrated the effective inhibitory of the Ni(II)-complex relative to other tested compounds. The antimicrobial activity of the compounds suggests that Cr(III) has the highest activity. Furthermore, the Molecular Operating Environment (MOE) program was used to calculate the binding affinity between the EGFR protein and the compounds under investigation.

A Dimeric Thiourea CSA for the Enantiodiscrimination of Amino Acid Derivatives by NMR Spectroscopy.

The reaction of benzoyl isothiocyanate with (1R,2R)-1,2-bis(2-hydroxyphenyl)ethylenediamine afforded a new thiourea chiral solvating agent (CSA) with a very high ability to differentiate 1H and 13C NMR signals of simple amino acid derivatives, even at low concentrations. The enantiodiscrimination efficiency was higher with respect to that of the parent monomer, a thiourea derivative of 2-((1R)-1-aminoethyl)phenol, thus putting into light the relevance of the cooperativity between the two molecular portions of the dimer in a cleft conformation stabilized by interchain hydrogen bond interactions. An achiral base additive (DABCO or DMAP) played an active role in the chiral discrimination processes, mediating the interaction between the CSA and the enantiomeric mixtures. The chiral discrimination mechanism was investigated by NMR spectroscopy through the determination of complexation stoichiometries, association constants, and the stereochemistry of the diastereomeric solvates.

New Route to the Synthesis of Benzamide-Based 5-Aminopyrazoles and Their Fused Heterocycles Showing Remarkable Antiavian Influenza Virus Activity.

This study describes a new route to the synthesis of novel benzamide-based 5-aminopyrazoles and their corresponding pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c][1,2,4]triazine derivatives. Benzamide-based 5-aminopyrazoles were prepared through a reaction of benzoyl isothiocyanate with malononitrile in KOH–EtOH followed by alkylation with alkyl halides and then a reaction with hydrazine. In an attempt to react benzoyl isothiocyanate with ethyl cyanoacetate in KOH–EtOH followed by alkylation with methyl iodide at room temperature and then a reaction with hydrazine has resulted in the formation of 3-ethoxy-5-phenyl-1H-1,2,4-triazole. The structures of the new compounds were characterized by mass spectroscopy, 1H nuclear magnetic resonance (1H NMR) spectroscopy, infrared spectroscopy (IR), and X-ray analysis. The new compounds were tested in vitro for their anti-influenza A virus (subtype H5N1) activity. Among the synthesized compounds, eight compounds 3b, 4, 10b, 10c, 12a, 19, 21a, and 21b were found to possess significant antiviral activities against bird flu influenza (H5N1) with viral reduction in the range of 85–65%.

Synthesis, crystal structure and antioxidant evaluation of N-(4-formylpiperazine-1-carbonothioyl)benzamide

New benzoylthiourea derivative, N-(4-formylpiperazine-1-carbonothioyl)benzamide was prepared by the reaction of benzoylisothiocyanate with 1-piperazinecarboxaldehyde in acetone as solvent. The compound was characterized by FT-IR and multinuclear 1H and 13C NMR spectroscopy techniques. The benzoylthiourea molecule was obtained in crystalline form by recrystallization in DMSO. Single crystal X-ray diffraction study indicates that compound crystallized in triclinic crystal system and crystal data for C13H15N3O2S, space group P-1 (no. 2), a = 7.3016(9) Å, b = 7.7380(9) Å, c = 12.9815(16) Å, α = 103.581(4)°, β = 102.153(4)°, γ = 102.409(4)°, V = 669.46(14) Å3, Z = 2, T = 296(2) K, μ(MoKα) = 0.243 mm-1, Dcalc = 1.376 g/cm3, 31184 reflections measured (6.72° ≤ 2Θ ≤ 53.46°), 2822 unique (Rint = 0.0582) which were used in all calculations. The final R1 was 0.0501 (>2σ(I)) and wR2 was 0.1493 (all data). Intramolecular N-H···O hydrogen bond is stabilized the trans geometry of the thiono and the carbonyl groups. The heterocyclic piperazine ring makes a dihedral angle of 48.50(15)° with the benzene ring. Antioxidant test by DPPH method showed that compound exhibits good antioxidant activity of about 75%.

A New Synthetic Method for Tetraazatricyclic Derivatives and Evaluation of Their Biological Properties

AbstractA new method for the synthesis of tetraazatricyclic compounds by a reaction of benzoyl isothiocyanates with 2‐aminobenzimidazole is presented and a possible mechanism proposed. The new base‐catalyzed degradation of the tetraazatricyclic ring has been carried out. A reaction of benzoyl isothiocyanate with 2‐aminobenzoxazole, however, resulted in the formation of 3‐benzoyl‐1‐(2‐hydroxyphenyl)urea while a reaction with 2‐aminobenzothiazole gave 3‐(1,3‐benzothiazol‐2‐yl)‐1‐(benzoyl)thiourea. Density functional theory computed reaction mechanism for the formation of tetraazaatricyclic compounds is discussed. Biological screening of the compounds against Plasmodium falciparium and HIV‐1 protease showed very little activity but they were moderately active against Trypanosoma brucei with an IC50 of 19.71 μM for 11‐(3‐methoxyphenyl)‐1,8,0,12‐tetraazatricyclo [7.4.0.02,7]trideca‐2(7),3,5,9,11‐pentaene‐13‐thione (4).

Synthesis and characterization of p-dimethylaminobenzaldehyde benzoylthiourea and study towards selective and sensitive fluorescent sensor for detection of iron (III) cation in aqueous solution

Benzoyl thiourea derivatives ligand backbones contain Oxygen (O), Nitrogen (N), and Suphur (S) donor atoms can react with transition metal ions and form stable metal complexes. A new ligand was synthesized by the reaction of benzoyl isothiocyanate with diethylenetriamine and characterized by using Elemental Analysis (EA), Infrared (IR) spectroscopy and proton Nuclear Magnetic Resonance (1H NMR) spectroscopy. The monofunctionalize ligand were synthesized using 1:1 condensation of p-dimethylaminobenzaldehyde with diethylenetriamine and confirmed by disappearance of carbonyl group, C=O at 1656 cm-1 with the appearance of peak C=N in the range 1633 - 1638 cm-1 in the IR spectrum. This monofunctionalize ligand was synthesis by using Schiff base technique. Benzoyl thiourea derivatives, HN are synthesis from the 1:1 condensation of benzoyl isothiocyanates with monofunctionalized ligand. HN ligand was verified by the presence of peaks v(N-H), v(C=O), v(C=N) v(C-N) and v(C=S) at 3317 - 3336 cm-1, 1612 -1660 cm-1, 1550 -1589 cm-1, 1234-1366 cm-1 and 709-767 cm-1 respectively while 1H NMR show peaks of alkane (CH2), benzene (Ar-H), CONH, CSNH at 3.75, 6.73 – 7.33, 8.19, and 8.25 respectively. The total percent composition of C, H, N, O, and S using Elemental Analysis for HN, C21H27N5OS found was 85.23%. For application, further study on selectivity and sensitivity of HN ligand was conducted on several metal ions. The fluorescent emission spectroscopy shown that HN is a selective fluorescent sensor for Fe3+ and Cu2+ ions but not for other metal ions such as Co2+, Ni2+, Mn2+, Cr3+ and Zn2+. However, HN ligand shows more sensitive towards Fe3+ ions than Cu2+ ions which provide rapid detection of Fe3+ ions at concentrations as low as 4.5 x 10-7 M than 2.9 x 10-6 M of Cu2+ ions. As conclusion, HN ligand was expected to be useful as efficient chemical sensor for detection of Fe3+ ion.

Characterization of some amino acid derivatives of benzoyl isothiocyanate: Crystal structures and theoretical prediction of their reactivity

The reaction of benzoyl isothiocyanate with l-serine, l-proline, d-methionine and l-alanine gave 2-[(benzoylcarbamothioyl)amino]-3-hydroxypropanoic acid (I), 1-(benzoylcarbamothioyl)pyrrolidine-2-carboxylic acid (II), 2-[(benzoylcarbamothioyl)amino]-4-(methylsulfanyl)butanoic acid (III) and 2-[(benzoylcarbamothioyl)amino]propanoic acid (IV), respectively. The compounds have been characterized by IR, NMR, microanalyses and mass spectrometry. The crystal structures of all the compounds have also been discussed. Compound II showed rotamers in solution. DFT calculations of the frontier orbitals of the compounds have been carried out to ascertain the groups that contribute to the HOMO and LUMO, and to study their contribution to the reactivity of these compounds. The calculations indicated that the carboxylic acid group in these compounds is unreactive hence making the conversion to benzimidazoles via cyclization on the carboxylic acids impractical. This has been further confirmed by the reaction of compounds I–IV, respectively, with o-phenylene diamine which was unsuccessful but gave compound V.

Synthesis, Spectroscopic and Molecular Studies of Half‐Sandwich η6‐Arene Ruthenium, Cp* Rhodium and Cp* Iridium Metal Complexes with Bidentate Ligands

AbstractThe bidentate ligand benzoyl(2‐pyridyl)thiourea (L1) was prepared by reaction of benzoyl isothiocyanate with primary amine (2‐aminopyridine) but the reaction with secondary amine bis(2‐pyridyl)amine, yielded the unexpected product bis(2‐pyridyl)benzoylamine (L2). Mononuclear complexes of the general formula [(η6‐arene)Ru(L)Cl]+ {where, L = L1, arene = benzene (1); p‐cymene (2); L = L2, arene = benzene (5); p‐cymene (6)} and [Cp*M(L)Cl]+ {where, L = L1, M = Rh (3), Ir (4); L = L2, M = Rh (7), Ir (8)}, respectively, were formed by reaction of the ligands L1 and L2 with precursor complexes [(η6‐arene)Ru(μ‐Cl)Cl]2 and [Cp*M(μ‐Cl)Cl]2 (M = Rh, Ir). The cationic complexes were characterized by FT‐IR, UV/Vis, and 1H‐NMR spectroscopy as well as mass spectrometry. X‐ray crystallographic studies of these complexes reveal piano‐stool‐like arrangements around the metal atoms with six‐membered metallacycles in which L1 and L2 act as a N, S‐ and N, N' chelating ligands, respectively.

Synthesis, characterization, and crystal structure of bis[4-(3′-benzoyl)thiocarbamidophenyl]ether

The title compound, bis[4-(3′-benzoyl)thiocarbamidophenyl]ether, was synthesized by the reaction of benzoylisothiocyanate with 4,4′-diaminodiphenylether in aprotic solvent. The structure was determinated by means of elemental analysis and FT-IR, 1H-NMR, 13C-NMR and MS spectroscopic techniques. The crystal structure was characterized by X-ray syngle crystal analysis: orthorhombic, sp. gr. Pnna, Z = 4. In crystal packing, there are intramolecular hydrogen bond N-H⋯O generating S(6) motif, and intermolecular hydrogen bond N-H⋯S forming R22 (8) ring.

Synthesis and Characterization of Some Metals Complexes of {N-[(Benzoyl Amino)-Thioxo Methyl] Proline}

A new ligand {N-[(benzoyl amino)-thioxo methyl] proline} was prepared by the reaction of benzoyl isothiocyanate with proline. The ligand was characterized by FTIR, UV-Visible, and

새로운 아미노산 유도체인 N-[(Benzoyl amino)-Thioxomethyl]-Amino Acid(HL)의 착물 합성, 특성규명 및 생물학적 활성

benzoylisothiocyanate 와 아스파르트산 [BATA] (1), 글루탐산 [BATG] (2), 메티오닌 [BATM] (3), 루신 [BATL] (4), 및 트립토판 [BATT] (5) 등의 다양한 아미노산을 반응시켜 일련의 새로운 리간드인 N-[(benzoylamino)-thioxomethyl]-amino acid (HL)를 합성하였다. 이들 리간드의 특성을 원소분석, IR 및 NMR로 규명하였다. 이러한 리간드 (6-8)의 몇가지 전이금속 착물을 제조하여[M = Cu(II), Co(II), 또는 Ni(II)] 원소분석, IR 및 <TEX>$^1H$</TEX> NMR을 통하여 특성을 규명하였다. 항균성에 대한 연구 결과 모든 리간드가 항균 활성을 보이지 않는 반면, (<TEX>$ML_2$</TEX>) 착물; [M=Cu(II),Co(II), 또는 Ni(II)]은 (Gram -ive) Escherichia (NCTC5933) 및 (Gram +ive) Staphylococcus (NCTC6571)에 대해 항균 활성을 보였으며 또한 (BALB/C) 알비노 쥐에 대해 독성을 보이지 않았다. A new series of ligands N-[(benzoylamino)-thioxomethyl]-amino acid (HL) were synthesized by reaction of benzoylisothiocyanate with various amino acids namely aspartic acid [BATA] (1), glutamic acid [BATG] (2), methionine [BATM] (3), leucine [BATL] (4), and tryptophan [BATT] (5). The ligands were characterized by elemental analysis, IR and NMR spectra. Some transition metal complexes (<TEX>$ML_2$</TEX>) for these ligands (6-8) were prepared; [M=Cu(II), Co(II), or Ni(II)], and characterized by elemental analysis, IR and <TEX>$^1H$</TEX> NMR spectra. Antibacterial study showed that all the ligands have no antibacterial activity, whereas (<TEX>$ML_2$</TEX>) complexes; [M = Cu(II), Co(II), or Ni(II)] have antibacterial activity towards (Gram -ive) Escherichia (NCTC5933) and (Gram +ive) Staphylococcus (NCTC6571) and have no toxicity on (BALB/C) Albino mice.

Synthesis of 4H‐[1,3]Dithiolo[4,5‐b]pyrroles Through the Reaction of Benzoyl Isothiocyanate and Dialkyl Acetylenedicarboxylates in the Presence of Ph3P.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Synthesis of 4 H-[1,3]dithiolo[4,5- b]pyrroles through the reaction of benzoyl isothiocyanate and dialkyl acetylenedicarboxylates in the presence of Ph 3P

Benzoyl isothiocyanate reacts with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine in a mechanistically novel reaction to afford highly substituted dialkyl 2-(benzoylimino)-5-phenyl-4 H-[1,3]dithiolo[4,5- b]pyrrole-4,6-dicarboxylates with double insertion of the isothiocyanate. The reaction proceeds via a carbon to nitrogen migration of an alkoxycarbonyl group.

Synthesis and Characterization of N-benzoyl-N′-carboxyalkyl Substituted Thiourea Derivatives

N-Benzoyl-N'-carboxyl substituted thiourea derivatives (I-X) have been synthesized by the reaction of benzoyl isothiocyanate with amino acids. Their structures are confirmed by IR, 1 HNMR, and elemental analysis. The reaction conditions are experimentally investigated, and the preliminary biological tests show that some of the compounds have excellent plant growth promotion activities.

A Facile Synthesis of Substituted N-Benzoylthiourea

One pot reaction of benzoyl isothiocyanate and Tris(hydroxy- methyl)aminomethane (Tris) at room temperature with polyethylene glycol-400 (PEG-400) as solid–liquid phase-transfer catalyst produced substituted N-benzoylthioureas with high yield. A reasonable pathway for their formation has been suggested.

Reactions of Benzoylisothiocyanate with Acetoacetanilide: Synthesis of Pyrazole, Pyridine, Pyrimidine, Pyrazolo[3,4-d]pyrimidine, Pyrazolo[4,3-d]pyrimidine and Pyrido[4,3-d]oxazine Derivatives

We describe in this article the results of investigations involving the reaction of benzoyl isothiocyanate I with acetoacetanilides IIa, IIb.

Complexes of copper(II) with some new thiocarbamide derivatives

A new series of thiocarbamides was prepared by the reaction of benzoylisothiocyanate with various amines namely 2-aminopyridine (H2LI), 3-aminopyridine (H2LII), 2,3-diaminopyridine (H2LIII), 2,6-diaminopyridine (H2LIV), o-phenylene diamine (H2LV), p-phenylenediamine (H2LVI) and ethylene diamine (H2LVII). The copper(II) complexes of these ligands were isolated and have been characterized by elemental analyses, molar conductivities, magnetic moments and spectral (visible, i.r.) measurements. I.r. spectra show that the ligands behave as dianionic or neutral tetradentates or as monoanionic or neutral bidentates. The [Cu(HLI)Cl]2 and Cu(H2LIV)Cl2 complexes are diamagnetic and the other complexes have normal magnetic moment at room temperature. Electronic spectral analyses show that Cu2(LIV)Ac2 is planar and the other complexes are tetragonally distorted octahedral. All the complexes are non-electrolytes.

ChemInform Abstract: Reaction of Benzoyl Isothiocyanate with Active Methylene Reagents: A Convenient Synthesis of Pyrazolo(5,4‐c)pyrazole, 1,3‐Oxazine, Thiazole and Pyrimidine Derivatives.

AbstractBenzoyl isothiocyanate (I) reacts with the sodium salts of ethyl cyanoacetate (II), malononitrile (V) and acetylacetone (VI) to form the 1:1 adducts (III), (IV), and (VII).

Reaction of Benzoyl Isothiocyanate With Active Methylene Reagents: A Convenient Synthesis of Pyrazolo[5,4-c]pyrazole, 1,3-Oxazine, Thiazole and Pyrimidine Derivatives

Benzoyl isothiocyanate reacts with active methylene reagents e.g. ethyl cyanoacetate, malonitrile and acetylacetone to give, in each case, the corresponding 1:1 adduct 1, 13 and 14 respectively, Compound 1 was utilized for the synthesis of several heterocyclic derivatives. Compound 14 undergoes ready cyclization in basic medium to give the 1,3-oxazine derivative 15. The structures of the products were assigned and confirmed on the basis of their elemental analysis and spectral data.