(<i>E</i>)-5-Chloro-3-(2,6-dichlorobenzylidene)indolin-2-one

Zhang, Hongming; Ankati, Haribabu; Akubathini, Shashidhar Kumar; Biehl, Edward R.

doi:10.1107/s1600536808031930

Cited by 3 publications

(6 citation statements)

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“…13C NMR (500 MHz, DMSO-d6) 168.5 (CO), 147.6 (C), 143. 10.82 (s,1H,8.59 (s,2H,6'),7.90 (s,1H,7.85 (s,1H,7.75 (d,J = 6.85 Hz,1H,7.23 (d,J = 8.60 Hz,1H,6.81 (d,J = 8.60 Hz,1H,; NOE between H-vinyl and H-4; 13C NMR (500 MHz, DMSO-d6) 168.2 (CO), 141.9 (C), 138. (E)-2,6-Dibromo-4-(5'-chloro-2'-oxoindolin-3-ylidene) methyl)phenyl acetate (9) was obtained as a light brown solid; mp 148-150 oC.…”

Section: Synthesis Of 3-(hetaryl-2-methyl)indoline-2-onesmentioning

confidence: 99%

“…(Z-3-(2'-Nitrobenzylidene)indolin-2-one (6) was obtained as a light red solid; mp 239-241 oC. 1H NMR (500 MHz, DMSO-d6) 10.70 (s,1H,8.30 (d,1H,J = 8.0 Hz,4H,5',7.29 (t,J = 7.2 Hz,1H,3H,6,7). 13C NMR (500 MHz, DMSO-d6) 168.5 (CO), 147.6 (C), 143.…”

Section: Synthesis Of 3-(hetaryl-2-methyl)indoline-2-onesmentioning

confidence: 99%

“…(E)-2,6-Dibromo-4-(5'-chloro-2'-oxoindolin-3-ylidene) methyl)phenyl acetate (9) was obtained as a light brown solid; mp 148-150 oC. 1H NMR (500 MHz, DMSO-d6) 10.80 (s,1H,7.84 (s,2H,6'),7.52 (s,1H,Hvinyl),6.68 (s,1H,6.64 (d,J = 8.45 Hz,1H, (E)-3-Benzylidene-5-chloroindolin-2-one (12) was obtained as a yellow solid; mp 208-211 oC. 1H NMR (400 MHz DMSO-d6) 10.76 (s, 1H, NH-1), 7.68-7.73 (m, 3H, H-2',6', vinyl), 7.53-7.56 (m, 3H, H-3', 5',4) (E)-5-Chloro-3-(4'-methoxybenzylidene)indolin-2-one (14) was obtained as a yellow solid; mp 257-260 oC.…”

Section: Synthesis Of 3-(hetaryl-2-methyl)indoline-2-onesmentioning

confidence: 99%

“…1H NMR (400 MHz DMSO-d6) 10.76 (s, 1H, NH-1), 7.68-7.73 (m, 3H, H-2',6', vinyl), 7.53-7.56 (m, 3H, H-3', 5',4) (E)-5-Chloro-3-(4'-methoxybenzylidene)indolin-2-one (14) was obtained as a yellow solid; mp 257-260 oC. 1H NMR (400 MHz, 10.69 (s,1H,7.69 (d,J = 8.48 Hz,2H,6'),7.54 (d,J = 8.0 Hz,1H,7.25 (s,1H,7.15 (t,J = 8.0 Hz,1H,7.10 (d,J = 8.50 Hz,2H,5'),2H,5'),3.83 (s,3H,OCH3); 13C NMR (400 MHz, 169.4 (CO), 161. (E)-5-Chloro-3-(4'-(dimethylamino)benzylidene)indolin-2-one (15) was obtained as a orange solid; mp 257-260 oC.…”

Section: Synthesis Of 3-(hetaryl-2-methyl)indoline-2-onesmentioning

confidence: 99%

“…The purified isomeric mixtures were dissolved into DMSO-d 6 and their 1 H NMR spectrum were obtained as quickly as possible (usually within 2 min after mixing). NMR spectrum were then obtained at 1 h intervals.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 3- Benzylidene, 5-Substituted 3-Benzylidene, 3-Hetarylmethylene and 5-Substituted Hetarylmethylene Derivatives of Indolin-2-ones

Ankati¹,

Akubathini²,

Kamila³

et al. 2009

TOOCJ

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A wide variety of titled compounds, several of which have neuro-protecting properties has been prepared in yields ranging between 70 to 90%. The compounds were identified by 1 HNMR, 13 C NMR, 1D and 2D NOE analysis, and HRMS. An investigation of the effect of certain 5-substitutuents on the E to Z ratios in DMSO-d 6 was carried out. The 5-nitro and 5-acetyl substituents were not isomerized, whereas the 5-fluoro, 5-chloro and 5-bromo underwent significant isomerization. In the former cases resonance interaction of the lone pair electrons of NH group of the indolin-2-one with the 5-nitro or 5-acetyl of the indolin-2-one prevents rotation of the benzylidene C=C bond whereas in the case of the latter 5-halo substituent, the lone pair electrons on the NH group interacts with the benzylidene C=C bond giving rise to anionic C-C -bond in which rotation about this bond can occur.

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Section: Synthesis Of 3-(hetaryl-2-methyl)indoline-2-onesmentioning

confidence: 99%

Section: Synthesis Of 3-(hetaryl-2-methyl)indoline-2-onesmentioning

confidence: 99%

Section: Synthesis Of 3-(hetaryl-2-methyl)indoline-2-onesmentioning

confidence: 99%

Section: Synthesis Of 3-(hetaryl-2-methyl)indoline-2-onesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of 3- Benzylidene, 5-Substituted 3-Benzylidene, 3-Hetarylmethylene and 5-Substituted Hetarylmethylene Derivatives of Indolin-2-ones

Ankati¹,

Akubathini²,

Kamila³

et al. 2009

TOOCJ

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(Z)-5-Fluoro-3-[(1H-pyrrol-2-yl)methylene]indolin-2-one

et al. 2008

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The title compound, C13H9FN2O, a potential neuroprotective agent, consists of an indolinone and a pyrrolyl unit [dihedral angle between the ring planes = 4.9 (1)°]. An intramolecular hydrogen bond between the carbonyl O atom and the NH group of pyrrole correlates with the Z arrangement of the substituents at the C=C bond. In the crystal, inversion dimers occur, linked by pairs of N—H⋯O bonds.

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(Z)-3-[(E)-3-Phenylallylidene]indolin-2-one

et al. 2009

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(E)-5-Chloro-3-(2,6-dichlorobenzylidene)indolin-2-one

Abstract: There are two independent molecules of the title compound, C15H8Cl3NO, in the asymmetric unit. Both form inversion dimers via pairs of hydrazide–carbonyl N—H⋯O hydrogen bonds.

Cited by 3 publications

References 8 publications

Synthesis of 3- Benzylidene, 5-Substituted 3-Benzylidene, 3-Hetarylmethylene and 5-Substituted Hetarylmethylene Derivatives of Indolin-2-ones

Synthesis of 3- Benzylidene, 5-Substituted 3-Benzylidene, 3-Hetarylmethylene and 5-Substituted Hetarylmethylene Derivatives of Indolin-2-ones

(Z)-5-Fluoro-3-[(1H-pyrrol-2-yl)methylene]indolin-2-one

(Z)-3-[(E)-3-Phenylallylidene]indolin-2-one

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(E)-5-Chloro-3-(2,6-dichlorobenzylidene)indolin-2-one

Abstract: There are two independent mol­ecules of the title compound, C15H8Cl3NO, in the asymmetric unit. Both form inversion dimers via pairs of hydrazide–carbonyl N—H⋯O hydrogen bonds.

Cited by 3 publications

References 8 publications

Synthesis of 3- Benzylidene, 5-Substituted 3-Benzylidene, 3-Hetarylmethylene and 5-Substituted Hetarylmethylene Derivatives of Indolin-2-ones

Synthesis of 3- Benzylidene, 5-Substituted 3-Benzylidene, 3-Hetarylmethylene and 5-Substituted Hetarylmethylene Derivatives of Indolin-2-ones

(Z)-5-Fluoro-3-[(1H-pyrrol-2-yl)methylene]indolin-2-one

(Z)-3-[(E)-3-Phenylallylidene]indolin-2-one

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Abstract: There are two independent molecules of the title compound, C15H8Cl3NO, in the asymmetric unit. Both form inversion dimers via pairs of hydrazide–carbonyl N—H⋯O hydrogen bonds.