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

Subbulakshmi, Karanth N. and Narayana, B. and Yathirajan, H. S. and Akkurt, Mehmet and Celik, Ömer and Ersanlı, Cem Cüneyt and Glidewell, Christopher (2015) Di­hydro­oxazolones and di­hydro­imidazolo­nes derived from acyl­glycines: syntheses, mol­ecular structures and supra­molecular assembly. Acta Crystallographica Section C, 71 (8). pp. 742-751. ISSN 2053-2296

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Official URL: https://doi.org/10.1107/S2053229615013637


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 C22(14) chains. Compounds (III) and (IV) both form centrosymmetric R22(10) dimers built from N—H⋯O hydrogen bonds, while compound (V) forms a centrosymmetric R22(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.

Item Type: Article
Uncontrolled Keywords: oxazolones, imidazolones, orientational disorder, crystal structure, hydrogen bonding, Erlenmeyer azlactones, supramolecular assembly
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: MUL SWAPNA user
Date Deposited: 06 Nov 2019 05:17
Last Modified: 18 Dec 2019 11:29
URI: http://eprints.uni-mysore.ac.in/id/eprint/9821

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