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Catalyst and Solvent-Free Microwave Assisted Expeditious Synthesis of 3-Indolyl-3-hydroxy Oxindoles and Unsymmetrical 3,3-Di(indolyl)indolin-2-ones  [PDF]
Prasanna K. Vuram, C. Kabilan, Anju Chadha
International Journal of Organic Chemistry (IJOC) , 2015, DOI: 10.4236/ijoc.2015.52012
Abstract: A simple and efficient method for the synthesis of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-di(indolyl)indolin-2-ones using microwave irradiation without catalyst and solvent is described. A series of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-di(indolyl)indolin-2-ones have been synthesized in very short reaction times of 5 and 10 minutes and in yields ranging from 31% to 98% and from 53% to 78% respectively. This method offers a significant advantage over the conventional methods in terms of simplicity and shorter reaction time. To the best of our knowledge compounds N-allyl-3-hydroxy-3-(1-methyl-indol-3-yl)indolin-2-one (6c), N-allyl-3-hydroxy-3-(5-methoxy-indol-3-yl)indolin-2-one (8c), N-benzyl-3-hydroxy-3-(1-methyl-indol-3-yl) indolin-2-one (10c), N-propargyl-3-hydroxy-3-(1-methyl-indol-3-yl)indolin-2-one (13c), N-propargyl-3-hydroxy-3-(5-methoxy-indol-3-yl)indolin-2-one (14c), 3-(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (1e), 3-1-methyl(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (2e), 3-1-allyl(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (3e), 3-1-benzyl(5-methoxy-1H-in- dol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (4e) and 3-1-(prop-2-ynyl)(5-methoxy-1H-indol-3-yl)-3(1H-indol-3-yl)indolin-2-one (5e) are reported here for the first time. All the compounds are characterized by IR, 1H, 13C NMR and HRMS.
3-Hydroxy-3-[(2-methylpropanoyl)methyl]indolin-2-one
Gang Chen,Bin Liu,Ying Tang,Jingfang Xu
Acta Crystallographica Section E , 2009, DOI: 10.1107/s1600536809024611
Abstract: The title compound, C13H15NO3, was synthesized by the Aldol reaction of isatin and 3-methylbutan-2-one refluxing in methanol catalyzed by dimethylamine. The packing of the molecules in the crystal structure features intermolecular N—H...O and O—H...O hydrogen bonds.
6-Hydroxy-3-(hydroxyimino)indolin-2-one
Hui-ling Yu
Acta Crystallographica Section E , 2009, DOI: 10.1107/s1600536809034321
Abstract: In the title compound, C8H6N2O3, the indol-2-one system is almost planar [maximum deviation = 0.010 (3) ]. In the crystal structure, intermolecular N—H...O, O—H...N and O—H...O hydrogen bonds link the molecules into a three-dimensional network. π–π contacts between the indole ring systems [centroid–centroid distances = 3.494 (1), 3.731 (1) and 3.736 (1) ] may further stabilize the structure.
Spiro[indene-1,1′-benzo[e]indolin]-2′-one  [cached]
Jin-Xiang Chen,Yu-Qin Wang,Shu-Wen Liu,Wei-Er Lin
Acta Crystallographica Section E , 2011, DOI: 10.1107/s1600536810049809
Abstract: In the title compound, C20H13NO, the indene ring is disordered over two sites with an occupancy ratio of 0.557 (2):0.443 (2). Both disordered components of indene are nearly perpendicular to the naphthalene ring system, making dihedral angles of 90.9 (2) and 85.0 (5)°. The five-membered ring of the 1H-pyrrol-2(3H)-one adopts an envelope conformation with the spiro C atom at the flap position. Intermolecular classical N—H...O and weak C—H...O hydrogen bonding is present in the crystal structure.
1-(2,6-Dichlorophenyl)indolin-2-one
Muhammad Hanif,Muhammad Rafiq,Muhammad Saleem,Ghulam Qadeer
Acta Crystallographica Section E , 2009, DOI: 10.1107/s1600536809005807
Abstract: In the molecule of the title compound, C14H9Cl2NO, the planar indole ring system [with a maximum deviation of 0.020 (2) for the N atom] is oriented at a dihedral angle of 72.17 (3)° with respect to the phenyl ring. In the crystal structure, weak intermolecular C—H...O hydrogen bonds link the molecules. A weak C—H...π interaction may further stabilize the structure.
(E)-3-(2,6-Dichlorobenzylidene)indolin-2-one
Hongming Zhang,Haribabu Ankati,Ed Biehl
Acta Crystallographica Section E , 2009, DOI: 10.1107/s1600536809043487
Abstract: There are two independent molecules in the asymmetric unit of the title compound, C15H9Cl2NO. The dihedral angles between the oxindolyl and dichlorophenyl rings are essentially identical for the two independent molecules [63.4 (1) and 63.2 (1)°]. Dimers linked by amide–carbonyl N—H...O hydrogen bonds are formed from each symmetry-independent molecule and the respective symmetry equivalent created by inversion.
Spiro[cyclopropane-1,3′-indolin]-2′-one  [cached]
Maosen Yuan,Qi Wang,Yuejun Zhang,Junru Wang
Acta Crystallographica Section E , 2011, DOI: 10.1107/s1600536811034167
Abstract: In the title molecule, C10H9NO, the dihedral angle between the mean plane of the cyclopropane ring and the essentially planar [maximum deviation = 0.032 (2) ] indole ring system is 87.65 (17)°. In the crystal, intermolecular N—H...O hydrogen bonds link molecules into one-dimensional chains along [100].
Spiro[1,3-dioxolane-2,3′-indolin]-2′-one
Yan Meng,Yanqing Miao
Acta Crystallographica Section E , 2010, DOI: 10.1107/s1600536810016132
Abstract: The title compound, C10H9NO3, was synthesized by the condensation reaction of isatin (systematic name 1H-indole-2,3-dione) with glycol in presence of p-toluenesulfonic acid. The indol-2-one ring system is essentially planar [N—C—C—C torsion angle = 3.1 (2)°], and the 1,3-dioxolane ring is slightly distorted. The crystal structure exhibits intermolecular N—H...O hydrogen bonds.
Synthesis and Physical Characterization of 2-((E)-1-(3-((E)-1-(2-hydroxyphenyl)ethylideneamino)-2-methylphenylimino)ethyl)phenol  [PDF]
A. A. Jarrahpour,A. F. Jalbout,S. Rezaei,B. Trzaskowski
Molbank , 2006, DOI: 10.3390/m455
Abstract: In this paper we propose the synthesis of 2-((E)-1-(3-((E)-1-(2-hydroxyphenyl) ethylideneamino)-2-methylphenylimino) ethyl) phenol. In addition to its synthesis we present AM1 and B3LYP/6-31G* calculations to characterize the physical properties of the molecule.
One pot synthesis of 2-hydroxy pyrrolidine derivatives  [PDF]
Putta. P. Varma,Kittappa. M. Mahadevan,Abdul Khader,Vijaykumar Hulikal
Organic Communications , 2011,
Abstract: One pot reaction of various 2-amino-thiadiazoles or thiazoles and 2,3- dihydrofuran under mild condition in presence of CeCl 3.7H 2O as catalyst transformed the amino group of 2-amino-thiadiazoles or thiazoles into a medicinally important 2-hydroxy pyrrolidine ring system in good to excellent yields. The generality of the reaction was sufficiently investigated and demonstrated. The new reaction path way for this conversion was established by spectroscopic and analytical methods.
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