Benzoid–Quinoid tautomerism of schiff bases and their structural analogs: LVII. 2-[(3-oxo-5-phenylpyrazolidin-1-yl)methylidene]-1H-indene-1,3(2H)-dione

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• 作者：O. S. Popova ; V. A. Bren’ ; V. V. Tkachev…
• 刊名：Russian Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：52
• 期：4
• 页码：541-545
• 全文大小：385 KB
• 刊物主题：Organic Chemistry;
• 出版者：Springer US
• ISSN：1608-3393
• 卷排序：52

文摘

Potentially tautomeric azomethine imide, 2-[(3-oxo-5-phenylpyrazolidin-1-yl)methylidene]-1H-indene- 1,3(2H)-dione, has been synthesized by condensation of 5-phenylpyrazolidin-3-one with 2-(hydroxymethylidene)-1H-indene-1,3(2H)-dione. According to the IR, 1H and 13C NMR, and electronic absorption spectroscopy data and DFT B3LYP/6-311++G(d,p) quantum chemical calculations, the title compound in solution exists as planar tricarbonyl tautomer stabilized by intramolecular hydrogen bond between the NH proton of the pyrazolidine fragment and carbonyl oxygen atom of the indene fragment. Its crystal structure was determined by X-ray analysis.Original Russian Text © O.S. Popova, V.A. Bren’, V.V. Tkachev, A.N. Utenyshev, Yu.V. Revinskii, K.S. Tikhomirova, A.G. Starikov, G.S. Borodkin, A.D. Dubonosov, I.E. Tolpygin, G.V. Shilov, S.M. Aldoshin, V.I. Minkin, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 4, pp. 555–559.