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

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dc.authoridAkkurt, Mehmet/0000-0003-2421-0929
dc.authoridCELIK, OMER/0000-0003-2633-4458
dc.authoridCelik, Omer/0000-0002-3314-6132
dc.authoridERSANLI, CEM CUNEYT/0000-0002-8113-5091
dc.contributor.authorSubbulakshmi, Karanth N.
dc.contributor.authorNarayana, Badiadka
dc.contributor.authorYathirajan, Hemmige S.
dc.contributor.authorAkkurt, Mehmet
dc.contributor.authorCelik, Omer
dc.contributor.authorErsanli, Cem Cuneyt
dc.contributor.authorGlidewell, Christopher
dc.date.accessioned2025-03-23T19:32:12Z
dc.date.available2025-03-23T19:32:12Z
dc.date.issued2015
dc.departmentSinop Üniversitesi
dc.description.abstractSyntheses 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-1en-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 center dot center dot center dot O hydrogen bonds to form C-2(2)(14) chains. Compounds (III) and (IV) both form centrosymmetric R-2(2)(10) dimers built from N-H center dot center dot center dot O hydrogen bonds, while compound (V) forms a centrosymmetric R-2(2)(10) dimer built from C-H center dot center dot center dot O hydrogen bonds. In the structure of compound (VI), a combination of N-H center dot center dot center dot O and C-H center dot center dot center dot pi (arene) hydrogen bonds links the molecules into sheets. Comparisons are made with some similar compounds.
dc.description.sponsorshipUGC through BSR
dc.description.sponsorshipThe authors are indebted to the X-ray laboratory of Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. BN acknowledges the financial assistance of UGC through a BSR one-time grant for the purchase of chemicals. KNS gratefully acknowledges the Department of Chemistry, Shri Madhwa Vadiraja Institute of Technology, Bantakal (VTU, Belgaum), for providing access to research facilities.
dc.identifier.doi10.1107/S2053229615013637
dc.identifier.endpage+
dc.identifier.issn2053-2296
dc.identifier.pmid26243425
dc.identifier.scopus2-s2.0-84952759999
dc.identifier.scopusqualityN/A
dc.identifier.startpage742
dc.identifier.urihttps://doi.org/10.1107/S2053229615013637
dc.identifier.urihttps://hdl.handle.net/11486/5444
dc.identifier.volume71
dc.identifier.wosWOS:000359195500019
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherInt Union Crystallography
dc.relation.ispartofActa Crystallographica Section C-Structural Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectoxazolones
dc.subjectimidazolones
dc.subjectorientational disorder
dc.subjectcrystal structure
dc.subjecthydrogen bonding
dc.subjectErlenmeyer azlactones
dc.subjectsupramolecular assembly
dc.titleDihydrooxazolones and dihydroimidazolones derived from acylglycines: syntheses, molecular structures and supramolecular assembly
dc.typeArticle

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