(<i>E</i>)-4-(2,5-Dimethoxybenzylidene)-2-phenyl-1,3-oxazol-5(4<i>H</i>)-one

Asiri, Abdullah M.; Ng, Seik Weng

doi:10.1107/s1600536809024593

Cited by 5 publications

(4 citation statements)

References 8 publications

(7 reference statements)

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“…The non-bonding distance Cl1-H7A is 2.565(3) Å, which is much shorter than the sum of the van der Waals radii (2.95 Å) [51]. The same syn arrangement between the ortho-substituent and the benzylidene proton has also been observed in related orthosubstituted unsaturated 4-arylidene-oxazolones [52][53][54][55][56][57][58][59]. The internal bond distances and angles for the 4-arylidene fragment and the oxazolone ring are similar or identical, within experimental error, to those found in related oxazolones reported in the literature [52][53][54][55][56][57][58][59].…”

Section: Resultsmentioning

confidence: 86%

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Urriolabeitia¹,

Sánchez²,

Pop³

et al. 2020

Beilstein J. Org. Chem.

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The stereoselective synthesis of truxillic bis-amino esters from polyfunctional oxazolones is reported. The reaction of 4-((Z)-arylidene)-2-(E)-styryl-5(4H)-oxazolones 2 with Pd(OAc)2 resulted in ortho-palladation and the formation of a dinuclear open-book complexes 3 with carboxylate bridges, where the Pd atom is C^N bonded to the oxazolone. In 3 the two exocyclic C=C bonds of the oxazolone are in a face-to-face arrangement, which is optimal for their [2 + 2] photocycloaddition. Irradiation of dimers 3 in CH2Cl2 solution with blue light (465 nm) promoted the chemo- and stereoselective [2 + 2] photocycloaddition of the exocyclic C=C bonds and the formation of cyclobutane-containing ortho-palladated complexes 4. Treatment of 4 with CO in a MeOH/NCMe mixture promoted the methoxycarbonylation of the palladated carbon and the release of the corresponding ortho-functionalized 1,3-diaminotruxillic bis-amino esters 5 as single isomers.

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Section: Resultsmentioning

confidence: 86%

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Urriolabeitia¹,

Sánchez²,

Pop³

et al. 2020

Beilstein J. Org. Chem.

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“…The two independent molecules differ in their supramolecular aggregation, although both form C-HÁ Á ÁO hydrogen bonds; molecules of one type are linked into centrosymmetric dimers, as in (VII) and (VIII), while molecules of the second type are linked into chains. For compound (X), which crystallizes with Z 0 = 2 in the space group P1, the supramolecular assembly is not mentioned in the original report (Asiri & Ng, 2009). In fact, molecules of one type, related by translation, are linked by C-HÁ Á ÁO hydrogen bonds to form C(9) chains, from which the molecules of the other type are pendent (Fig.…”

Section: Tablementioning

confidence: 99%

“…A stereoview of part of the crystal structure of compound (X), showing the formation of a hydrogen-bonded C(9) chain built from one type of molecule, from which molecules of the second type are pendent. The original atomic coordinates (Asiri & Ng, 2009) have been used and, for the sake of clarity, H atoms not involved in the motif shown have been omitted. For all compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction:…”

Section: Figure 12mentioning

confidence: 99%

Dihydrooxazolones and dihydroimidazolones derived from acylglycines: syntheses, molecular structures and supramolecular assembly

et al. 2015

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Syntheses and structures are described for some alkylidene-substituted dihydrooxazolones and dihydroimidazoles derived from simple acylglycines. A second, triclinic, polymorph of 4-benzylidene-2-(4-methylphenyl)-1,3-oxazol-5(4H)-one, C17H13NO2, (I), has been identified and the structure of 2-methyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one, C9H7NO2S, (II), has been rerefined taking into account the orientational disorder of the thienyl group in each of the two independent molecules. The reactions of phenylhydrazine with 2-phenyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one or 2-(4-methylphenyl)-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one yield, respectively, 3-anilino-2-phenyl-5-[(thiophen-2-yl)methylidene]-3,5-dihydro-4H-imidazol-4-one, C10H15N3OS, (III), and 3-anilino-2-(4-methylphenyl)-5-[(thiophen-2-yl)methylidene]-3,5-dihydro-4H-imidazol-4-one, C21H17N3OS, (IV), which both exhibit orientational disorder in their thienyl groups. The reactions of 2-phenyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one with hydrazine hydrate or with water yield, respectively, N-[3-hydrazinyl-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl]benzamide and 2-(benzoylamino)-3-(thiophen-2-yl)prop-2-enoic acid, which in turn react, respectively, with thiophene-2-carbaldehyde to form 2-phenyl-5-[(thiophen-2-yl)methylidene]-3-{[(E)-(thiophen-2-yl)methylidene]amino}-3,5-dihydro-4H-imidazol-4-one, C19H13N3OS2, (V), which exhibits orientational disorder in only one of its thienyl groups, and with methanol to give methyl (2Z)-2-(benzoylamino)-3-(thiophen-2-yl)prop-2-enoate, C15H13NO3S, (VI). There are no direction-specific intermolecular interactions in the crystal structure of the triclinic polymorph of (I), but the molecules of (II) are linked by two independent C-H···O hydrogen bonds to form C2(2)(14) chains. Compounds (III) and (IV) both form centrosymmetric R2(2)(10) dimers built from N-H···O hydrogen bonds, while compound (V) forms a centrosymmetric R2(2)(10) dimer built from C-H···O hydrogen bonds. In the structure of compound (VI), a combination of N-H···O and C-H···π(arene) hydrogen bonds links the molecules into sheets. Comparisons are made with some similar compounds.

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“…Except the torsion angles, the bond parameters are comparable with the other oxazol-5-one derivatives. [28][29][30][31][32] N1/C3/C4/C5 torsion angles [-7.78(1) Å for 1 and 8.39(1) Å for 2] are slightly different. Also, as can be seen from the results, there is a good correlation between the experimental and theoretical data.…”

Section: Crystal Structurementioning

confidence: 99%

Spectroscopic, Structural and Density Functional Theory (DFT) Studies of Two Oxazol-5-one Derivatives

Nazlı

Celepci²,

Yakalı³

et al. 2018

ACSi

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In this study, two oxazol-5-one derivatives, C 20 H 20 N 2 O 2 (1) and C 21 H 22 N 2 O 2 (2), were synthesized by getting condensed p-N,N-diethylaminobenzaldehyde with two presented hippuric acid derivatives and in further studies they were analysed spectrochemically. Molecular and crystal structures of the compounds were determined by single-crystal X-ray diffraction and the results revealed that the molecular packing of the crystal structures were stabilized by weak intraand intermolecular interactions also with C-O•••π, C-H•••π and π•••π stacking interactions. Computational studies were also performed using DFT method at B3LYP/6-311G(d,p) level of theory. Vibrational modes and chemical shifts were calculated and compared with the experimental data. In addition, frontier molecular orbitals and molecular electrostatic potential surfaces were simulated. The calculated results show that the optimized geometries can well reproduce the crystal structure. Purpose of this study was to survey the effects of the reactants, which were condensed with each other to produce oxazol-5-one, upon the characteristic properties and crystal forms of the final oxazol-5-one.

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(E)-4-(2,5-Dimethoxybenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one

Cited by 5 publications

References 8 publications

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

Dihydrooxazolones and dihydroimidazolones derived from acylglycines: syntheses, molecular structures and supramolecular assembly

Spectroscopic, Structural and Density Functional Theory (DFT) Studies of Two Oxazol-5-one Derivatives

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