Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines<sup>1</sup>

Campaigne, E.; Verth, James E. Van

doi:10.1021/jo01103a029

Cited by 18 publications

(6 citation statements)

References 1 publication

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“…It has therefore been necessary to do a detailed investigation of the structure of these compounds by 'H, I3C and "N NMR spectroscopy. The oxamide derivatives were prepared from the reaction of oxalyl chloride and the corresponding aromatic compounds (1)(2)(3), norephedrine (4) or norpseudoephedrine (3).…”

Section: Methodsmentioning

confidence: 99%

“…for C,,jH,,N2O4: C,64.0;H,5.36; N, 9.33%); m.p. 252-254 "C. (3).-Aniline (5 g, 53.76 mmol) in THF (25 an3) was treated dropwise under vigorous stirring with oxalyl chloride (3.41 g, 26.88 mmol, 0.5 eq.) at 25 "C. After stirring for an additional 1 h at 25 "C, the reaction product 5 was obtained from the precipitate that was removed and washed with 95% ethanol.…”

Section: Nn'-bis[(z-hydroxy)phenyl)oxarnide (L)mentioning

confidence: 99%

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¹H,¹³C,¹⁵N, 2D and variable temperature NMR study of the role of hydrogen bonding in the structure and conformation of oxamide derivatives

Martínez‐Martínez¹,

Ariza‐Castolo²,

Tlahuext³

et al. 1993

J. Chem. Soc., Perkin Trans. 2

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The structure and conformation of N,N'-bis[(2-hydroxy)phenyl]oxamide (1 ); N,N'-bis[(2-methoxy)phenylloxamide (2); NN-bis(pheny1)oxamide (3); N,N'-bis[(l R,2S)-( -)-norephedrineloxamide (4); N,N'-bis[ (1 R,2R)-( -)-norpseudoephedrine]oxamide ( 5 ) ; N-[(2-hydroxy)phenyl]methylamide (6); N-[ (2-methoxy)phenyl]methylamide (7); N-phenylmethylamide (8); N-[ ( -) -norephedrine1methylamide ( 9 ) and N-[( -) -norpseudoephedrine]methylamide (1 0) were unambiguously established by 'H, 13C, 15N, 2 0 and variable temperature NMR spectroscopy. A careful NMR investigation of the conformational behaviour in these systems was relevant. It has been found that the dicarbonylic group in compounds 1-5 has a trans geometry, stabilized by intramolecular hydrogen bonding and that they possess a C2 axis. Compounds 1 and 2 are planar and compounds 1,2,4 and 5 present the amidic proton coordinated by two oxygen atoms.

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Section: Methodsmentioning

confidence: 99%

Section: Nn'-bis[(z-hydroxy)phenyl)oxarnide (L)mentioning

confidence: 99%

¹H,¹³C,¹⁵N, 2D and variable temperature NMR study of the role of hydrogen bonding in the structure and conformation of oxamide derivatives

Martínez‐Martínez¹,

Ariza‐Castolo²,

Tlahuext³

et al. 1993

J. Chem. Soc., Perkin Trans. 2

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“…The various quinoxalinedithiol derivatives were prepared according to methods registered in the literature [18][19][20][21] . Styrenedithiol and methylstyrenedithiol were used in the form of their 1,3-dithiol-2-thione (Fig.…”

Section: Methodsmentioning

confidence: 99%

“…al. 18 In a second Schlenk tube 1-pheny-l,2-methyl-1,3-dithiolium-2-thione (Fig. 2, R5 = CH3) (220 mg, 1 mmol), or the equivalent weight of 1-phenyl-1,3-dithiolium-2-thione (Fig.…”

Section: [Cp2ti(me-sdt)] and [Cp2ti(sdt)]mentioning

confidence: 99%

Syntheses and Electrochemical Studies of Bis(eta5-Cyclopentadienyl)-(2,3-Quinoxalinedithiolato)Titanium(IV) Derivatives: Comparison with the Electrochemical Properties of Similar Complexes

Lena¹,

Garner²

1998

J. Braz. Chem. Soc.

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Neste trabalho descreve-se a síntese de novos derivados bis(η 5 -ciclopentadienil)(2,3-quinoxalina-ditiolato)titanio(IV) e bis(η 5 -ciclopentadienil)(1-fenil)(2-metil)(1,2-etenoditiolato)titanio(IV). As propriedades redox destes compostos juntamente com as propriedades de bis(η 5 -ciclopentadienil)(ene-1,2-ditiolato)titanio(IV) similares foram medidas em soluções neutras. Todos os compostos exibiram uma redução reversível envolvendo um elétron, sendo que o potencial de redução é dependente da natureza do ligante ditiolato. Um segundo processo de redução é observado para os derivados de 2,3-quinoxalina. As propriedades destes últimos também foram estudadas em meio ácido e a presença de H + tem um pequeno efeito em ambos os processos, sugerindo que o mesmo tipo de evento ocorre sob as duas condições.In this work the syntheses of novel bis(η 5 -cyclopentadienyl)(2,3-quinoxaline-dithiolato)titanium(IV) derivatives and bis(η 5 -cyclopentadienyl)(1-phenyl)(2-methyl)(1,2-ethenedithiolato)titanium(IV) is described. The redox properties of these compounds along with the properties of similar bis(η 5 -cyclopentadienyl)(ene-1,2-dithiolato)titanium(IV) complexes are assessed in neutral solutions. All the compounds exhibited a reversible one electron reduction process, the potential at which the reduction occurs being dependent on the nature of the dithiolato ligand. A second reduction process is observed on the 2,3-quinoxaline derivatives. The properties of the latter are also assessed in acidic solution and the presence of H + has a small effect on both processes, suggesting that the same type of event occurs under both conditions.

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“…To a suspension of 2.59 mmol (500 mg) benzothiazole-2-carboxyhydrazide (BTCH) 26,27 in 15 mL of chloroform, 0.0025 mmol (248 mg) of furan-2-carbaldehyde was added and this mixture was kept in cold condition for 5-7 h. Excess solvent was distilled off and the resulting solid was recrystallized from methanol to give yellow coloured compound. Purity of the compound was checked by TLC using acetone: methanol (1:1) mobile phase.…”

Section: Synthesis Of N -[(Z)-furan-2-yl-methylidene]-13benzothiazolmentioning

confidence: 99%

Synthesis, spectral characterization, antimicrobial, DNA interactions and molecular modeling studies of metal complexes of 1, 3-benzothiazole carbohydrazone

et al. 2018

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The compound N-[(Z)-furan-2-ylmethylidene]-1,3-benzothiazole-2-carbohydrazone (FMBC) and its Cu (II), Ni (II) and Zn (II) complexes were synthesized and characterized by Mass, FT-IR, NMR, elemental analysis, TGA, ESR and SEM-EDX. Based on spectro-analytical data, geometries have been assigned to the metal complexes in which the FMBC acted as bidentate chelate in its mono dissociated form (pKa = 10.56). HyperChem 7.5 software was used for quantum chemical calculations using semi-empirical method. The eigenvalues of frontier orbitals and their corresponding contour maps of HOMO and LUMO for the title compound were computed by means of single point PM3 method. DNA binding of the synthesized complexes with calf thymus DNA was studied by spectrophotometry, fluorescence and viscosity techniques. From the experimental results, it is found that the complexes bind effectively to CT-DNA through an intercalative mode. Molecular docking studies with host DNA moiety inferred corroborative results for binding affinity of the compounds in accordance with experimental data. IC 50 values calculated from the cytotoxicity studies carried out on HeLa cell line by MTT assay inferred obviously enhanced activity of the metal complexes over unbound free ligand. The candidate compounds screened for antimicrobial activity against bacterial species Bacillus, Escherichia coli, Staphylococcus, Pseudomonas and fungal species Sclerotium rolfsii and Macrophomina phaseolina signified greater potency of metal complexes over free carbohydrazone ligand.

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Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines¹

Cited by 18 publications

References 1 publication

¹H,¹³C,¹⁵N, 2D and variable temperature NMR study of the role of hydrogen bonding in the structure and conformation of oxamide derivatives

¹H,¹³C,¹⁵N, 2D and variable temperature NMR study of the role of hydrogen bonding in the structure and conformation of oxamide derivatives

Syntheses and Electrochemical Studies of Bis(eta5-Cyclopentadienyl)-(2,3-Quinoxalinedithiolato)Titanium(IV) Derivatives: Comparison with the Electrochemical Properties of Similar Complexes

Synthesis, spectral characterization, antimicrobial, DNA interactions and molecular modeling studies of metal complexes of 1, 3-benzothiazole carbohydrazone

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Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines1

Cited by 18 publications

References 1 publication

1H,13C,15N, 2D and variable temperature NMR study of the role of hydrogen bonding in the structure and conformation of oxamide derivatives

1H,13C,15N, 2D and variable temperature NMR study of the role of hydrogen bonding in the structure and conformation of oxamide derivatives

Syntheses and Electrochemical Studies of Bis(eta5-Cyclopentadienyl)-(2,3-Quinoxalinedithiolato)Titanium(IV) Derivatives: Comparison with the Electrochemical Properties of Similar Complexes

Synthesis, spectral characterization, antimicrobial, DNA interactions and molecular modeling studies of metal complexes of 1, 3-benzothiazole carbohydrazone

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Reaction of Diethyl Oxalate with Some ortho-Substituted Anilines¹

¹H,¹³C,¹⁵N, 2D and variable temperature NMR study of the role of hydrogen bonding in the structure and conformation of oxamide derivatives

¹H,¹³C,¹⁵N, 2D and variable temperature NMR study of the role of hydrogen bonding in the structure and conformation of oxamide derivatives