cas 7746-36-3, 4-Nitro-2-phenylindole | Articles data ｜lookchem

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7746-36-3

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Synthesis of 4- and 6-substituted nitroindoles
Enolizable ketones react with m-nitroaniline in the presence of strong base such as t-BuOK to give 4- and 6-substituted nitroindoles. The reaction proceeds via oxidative nucleophilic substitution of hydrogen in m-nitroaniline with enolate anions in positions ortho to the amino group giving anionic σH adducts that are additionally stabilized by intramolecular interaction between the amino and the carbonyl group. Spontaneous oxidation of the σH adducts followed by the Bayer type condensation of the produced ortho-aminonitrobenzyl ketones gives 4- and 6-substituted nitroindoles. The scope of this reaction and its basic mechanistic features are discussed.
Moskalev, Nikolai,Barbasiewicz, Micha?,Ma?kosza, Mieczys?aw
p. 347 - 358
(2007/10/03)

Mild Synthesis of Polyfunctional Benzimidazoles and Indoles by the Reduction of Functionalized Nitroarenes with Phenylmagnesium Chloride
Phenylmagnesium chloride has been used for the conversion of selected nitroarenes into nitrenes. Their insertion into a neighboring sp2 C-H bond yielded functionalized heterocycles. A novel and mild synthesis of polyfunctional benzimidazoles and indoles is described.
Dohle, Wolfgang,Staubitz, Anne,Knochel, Paul
p. 5323 - 5331
(2007/10/03)

A novel method of indole ring system construction: One-pot synthesis of 4- and 6-nitroindole derivatives via base promoted reaction between 3- nitroaniline and ketones
Base promoted condensation of ketones RCOCH2R' with 3-nitroaniline results in formation of the corresponding 4- and 6-nitro-2-R-3-R'-indoles. This multistep process apparently includes oxidative nucleophilic substitution of hydrogen in the arom
Moskalev, Nikolai,Makosza, Mieczyslaw
p. 5395 - 5398
(2007/10/03)

Synthesis of Indoles via Ring Closure of 2-Alkylnitroaniline Derivatives.
A variety of nitroindoles have been prepared from imidate, amidine, and sec-anilide derivatives of 2-alkyl-3- or 5-nitroanilines by a base-induced cyclization promoted by dialkyl oxalates.It is shown that essentially the same procedure also can be used to synthesize the corresponding nitroindole-3-glyoxylates in one simple operation.The synthetic potential is discussed and a mechanism is proposed.
Bergman, Jan,Sand, Peter
p. 6085 - 6112
(2007/10/02)

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Chemical Properties

Boiling Point: 477.5 °C at 760 mmHg
Flash Point:242.6 °C
Density: 1.33 g/cm³
Storage Temp.:2-8°C
Vapor Pressure: 8.08E-09mmHg at 25°C
Refractive Index: 1.706
PSA: 61.61000
LogP: 4.26630

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