Síntese de 5-nitro-isatina e 5-cloro-isatina a partir da isonitrosoacetanilida

Silva, Bianca N. M. da; Bastos, Renato Saldanha; Silva, Bárbara V.; Pinto, Ângelo C.

doi:10.1590/s0100-40422010001000043

Cited by 16 publications

(10 citation statements)

References 10 publications

(14 reference statements)

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“…Initially, the nitration reaction of isatin 15 was performed, and the ketal dioxolane of 5-nitro-isatin was prepared from 5-nitro-isatin using ethylene glycol and p-TsOH in toluene. Then, the nitro group was reduced by catalytic hydrogenation to give the ketal dioxolane of 5-amine-isatin.…”

Section: Resultsmentioning

confidence: 99%

Ultrasound-Assisted Synthesis of Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions

Silva¹,

Pinto²,

Silva³

et al. 2016

Journal of the Brazilian Chemical Society

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This short report describes the preparation of twelve isatin derivatives, 5'-(4-alkyl/aryl-1H-1,2,3-triazoles), using 5-azido-spiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one in the presence of various alkynes under acidic conditions and ultrasound irradiation. Compared with conventional methods, yields increased to 78-98%, and reaction times decreased to 5 min. Besides time and energy saving, there was no need for purification of the product by column chromatography on silica gel, generating less waste and spent solvent.

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Section: Resultsmentioning

confidence: 99%

Ultrasound-Assisted Synthesis of Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions

Silva¹,

Pinto²,

Silva³

et al. 2016

Journal of the Brazilian Chemical Society

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“…Samples were analyzed in the solid state using the Attenuated Total Reflectance (ATR) accessory with diamond crystal. 1 H spectra were acquired in 5 mm NMR tubes at 298 K on a Bruker DPX 400 ( 1 H = 400.00 MHz) spectrometer. 1 H NMR chemical shifts were internally referenced to DMSO-d6 (ppm).…”

Section: Materials and Physical Methodsmentioning

confidence: 99%

“…Isatin (Figure 1a) is a heterocyclic compound which presents an aromatic ring joined to a second ring formed by ketonic and amidic groups. This configuration allows many modifications in its structure, such as addition of halogen atoms at C5 and C7 positions of the aromatic ring and alkylation/ acylation at N-H group which may lead to modifications of its chemical properties [1]. Isatins and their derivatives are known to have a broad spectrum of pharmacological applications such as antifungal, antibacterial, antiviral, antitumor, and antiprotozoal [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Nitroisatin dithiocarbazate: Synthesis, structural characterization, DFT, and docking studies

et al. 2021

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The reaction between 5-nitroisatin with S-benzyl dithiocarbazate affords a new isatindithio carbazate so-called NO2Isadtc (Benzyl 2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbodi thioate) which was characterized by means of 1H NMR, FT-IR, UV-visible and single crystal X-ray diffraction - Crystal data for C16H12N4O3S2 (M =372.42 g/mol): triclinic space group P-1, (n°. 02), a = 6.640 Å, b = 8.256 Å, c = 15.908 Å, V = 849.6 Å3, Z = 2, T = 293 K, μ(MoKα) = 0.337 mm-1, Dcalc = 1.456 g/cm3, 27515 reflections measured (2.499° ≤ 2Θ ≤ 26.524°), 3518 unique (Rint = 0.0533, Rsigma =0.0222) which were used in all calculations. The final R1 was 0.0367 (I > 2σ(I)) and wR2 was 0.1045 (all data). Computational methods were applied to NO2Isadtc and its nonsubstituted parent compound Isadtc for structure optimization, electronic distribution, and infrared calculations using B3LYP functional with 6-31G(d,p) basis set in ethanol as a polarizable continuum model. Furthermore, docking studies using human thioredoxin reductase 1 (TrxR) as enzyme target also were performed using NO2Isadtc and the optimized structure of Isadtc. The results demonstrated that both NO2Isadtc and Isadtc may act as inhibitors of TrxR, having different interactions detected, highlighting the contact between the NO2 group and the S111 at the helix which is found for NO2Isadtc.

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“…173–175 °C, lit . 175 °C . IR (cm −1 ): 3303, 3272, 3149, 1664, 1610, 1560, 1251, 1004, 904, 794, 694.…”

Section: Methodsmentioning

confidence: 99%

Rapid cleavage of phosphate triesters by the oxime 2‐(hydroxyimino)‐N‐phenyl‐acetamide

Manfredi

Demos

Wanderlind

et al. 2016

J of Physical Organic Chem

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We report the dephosphorylation reactions of the organophosphates diethyl 2,4-dinitrophenyl phosphate (DEDNPP) and dimethyl 4-nitrophenyl phosphate (methyl paraoxon) by the oxime 2-(hydroxyimino)-N-phenyl-acetamide (Ox 1). Rate enhancements of 10 7 -fold over the rate constant for the spontaneous hydrolysis are observed in aqueous medium in presence of the anionic form of the oxime. Ox 1 represents a new family of nucleophiles which could be used for the degradation of toxic organophosphates.

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Síntese de 5-nitro-isatina e 5-cloro-isatina a partir da isonitrosoacetanilida

Cited by 16 publications

References 10 publications

Ultrasound-Assisted Synthesis of Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions

Ultrasound-Assisted Synthesis of Isatin-Type 5'-(4-Alkyl/Aryl-1H-1,2,3-triazoles) via 1,3-Dipolar Cycloaddition Reactions

Nitroisatin dithiocarbazate: Synthesis, structural characterization, DFT, and docking studies

Rapid cleavage of phosphate triesters by the oxime 2‐(hydroxyimino)‐N‐phenyl‐acetamide

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