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

被引：0
|
作者：
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
机构：
[1] Southern Federal University,Research Institute of Physical and Organic Chemistry
[2] Russian Academy of Sciences,Institute of Chemical Physics Problems
[3] Russian Academy of Sciences,Southern Scientific Center
来源：
Russian Journal of Organic Chemistry | 2016年 / 52卷
关键词：
Methylidene; Indandione; Pyrazolidine; COSMO Model; Indene Fragment;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
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.
引用
收藏
页码：541 / 545
页数：4
相关论文
共 50 条
  • [41] Supramolecular Networks in Crystalline Inclusion Complexes Formed from a New Host: 2,2-Bis(4-hydroxy-3-phenylphenyl)-1H-indene-1,3(2H)-dione
    Kasugai, Kenta
    Hashimoto, Suzumi
    Imai, Kazunori
    Sakon, Aya
    Fujii, Kotaro
    Uekusa, Hidehiro
    Hayashi, Naoto
    Kobayashi, Keiji
    CRYSTAL GROWTH & DESIGN, 2011, 11 (09) : 4044 - 4052
  • [42] 2-(2′,3′-Dihydro-1′H-inden1′-yl)-1H-indene
    Jovanovic, J
    Schürmann, M
    Preut, H
    Spiteller, M
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2002, 58 : O33 - O34
  • [43] STRUCTURE OF 1H-ISOINDOLE-1,3(2H)-DIONE (PHTHALIMIDE)
    NG, SW
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 : 1694 - 1695
  • [44] IR spectra and structure of 1-H-isoindole-1,3(2H)-dione (phthalimide), cis-hexahydro-1-H-isoindole-1,3 (2H)-dione (hexahydrophthalimide) and of their nitranions
    Binev, IG
    Stamboliyska, BA
    Binev, YI
    Velcheva, EA
    Tsenov, JA
    JOURNAL OF MOLECULAR STRUCTURE, 1999, 513 (1-3) : 231 - 243
  • [45] Synthesis and antimicrobial activity of some 2-[1-(4-oxo-3,4-dihydrophthalazine-1-yl)alkyl]-1H-isoindole-1,3(2H)-dione and their imidoxy derivatives
    Salvi, Vijay K.
    Bhambi, Dinesh
    Jat, Jawahar L.
    Talesara, Ganpat L.
    ARKIVOC, 2006, : 133 - 140
  • [46] 5-Butylamino-2-[ 2-(dimethylamino)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione
    Xie, Li-Juan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1454 - U1788
  • [47] SUBSTITUTED 1-BENZOYL-1H-INDENE-1,3(2H)-DIONES WITH PHOTOPROTECTIVE ACTION
    SOFRONIEV, NV
    PETKOV, IN
    MINCHEV, S
    DOKLADI NA BOLGARSKATA AKADEMIYA NA NAUKITE, 1992, 45 (08): : 51 - 54
  • [48] 2-(1,1,2,2-tetrachloroethylsulfanyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione
    Chopra, D
    Mohan, TP
    Rao, KS
    Row, TNG
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 : O2406 - O2407
  • [49] Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione
    L. M. Gornostaev
    O. I. Fominykh
    T. I. Lavrikova
    Yu. G. Khalyavina
    Yu. V. Gatilov
    G. A. Stashina
    Russian Journal of Organic Chemistry, 2019, 55 : 1716 - 1725
  • [50] Synthesis and Crystal Structure of (S)-2-(3-Oxo-1,3-Dihydroisobenzofuran-1-yl)phthalazin-1(2H)-One
    Tai, Xishi
    Xue, Weixi
    2019 5TH INTERNATIONAL CONFERENCE ON ENVIRONMENTAL SCIENCE AND MATERIAL APPLICATION, 2020, 440
12345