78255-99-9Relevant academic research and scientific papers
A convenient one-pot access to phenanthridinones via Suzuki-Miyaura cross-coupling reaction
Tanimoto, Kouichi,Nakagawa, Naomichi,Takeda, Kazutaka,Kirihata, Mitsunori,Tanimori, Shinji
supporting information, p. 3712 - 3714 (2013/07/05)
A convenient one-step access to biologically important phenanthridinones 1 has been realized based upon Suzuki-Miyaura cross-coupling reaction. Reactions of 2-aminophenylboronic acid 2 with 2-halobenzoate 3 took place smoothly to afford substituted phenanthridinones 1 in excellent yields in the presence of palladium(II) acetate and 2-dicyclohexylphosphino-2′,6′- dimethoxybiphenyl (SPhos) as pre-catalysts. A natural product phenaglydon 1b was synthesized in one-pot manner from readily available starting materials in 95% yield.
General method for the synthesis of substituted phenanthridin-6(5H)-ones using a KOH-mediated anionic ring closure as the key step
Dubost, Emmanuelle,Magnelli, Rosa,Cailly, Thomas,Legay, Rémi,Fabis, Frédéric,Rault, Sylvain
experimental part, p. 5008 - 5016 (2010/08/13)
Substituted phenanthridin-6(5H)-ones were obtained in a two-step procedure involving a Suzuki cross-coupling reaction followed by a KOH-mediated anionic ring closure. The influence of the nature and the position of the substituents on the cyclization step were studied. This methodology offers a general and practical route to diversely substituted phenanthridin-6(5H)-ones.
Investigation of Phenanthridone and Its Derivatives by Infrared Spectroscopy
Val'kova, G. A.,Shifrina, R. R.,Shigorin, D. N.,Andrievskii, A. M.,Poplavskii, A. N.,Dyumaev, K. M.
, p. 537 - 538 (2007/10/02)
Infrared spectroscopy has been used to investigate phenanthridone and its 2-bromo, N-methyl-, and nitro-derivatives.It is shown that the vibration frequencies of the NH- and CO-groups depend on the nature of the substituents, their position in the molecule, the state of aggregation, and the polarity of the solvent.Substitution in the 2- and 8-positions has hardly any effect on the tendency of the lactam group to form intermolecular hydrogen bonds; in 3-nitrophenantridone they are weakened, while in 4- and 2, 4-dinitrophenanthridone only intramolecular hydrogen bonds are formed.
INVESTIGATION OF PHENANTHRIDONE AND DIOXOTETRAHYDRODIAZAPYRENE. 3. INVESTIGATION OF THE NITRATION OF 5H-PHENANTHRIDIN-6-ONE AND ITS DERIVATIVES
Migachev, G. I.,Grekhova, N. G.,Terent'ev, A. M.
, p. 289 - 294 (2007/10/02)
The nitration of 5H-phenanthridin-6-one (I), 5H-phenanthridin-6-one-10-carboxylic (II) and 5H-phenanthridin-6-one-1-carboxylic acids (III), 4H-cyclopentaphenanthridine-5,9-dione (IV), 4H-cyclopentaphenanthridine-5-one (V), 5,10-dioxo-4,5,9,10-tetrahydro-4,9-diazapyrene (VI), and 5,9-dioxo-4,5,9,10-tetrahydro-4,10-diazapyrene (VII) with nitric acid (sp. gr. 1.42-1.51) and a nitrating mixture of 0-120 deg C was investigated.The orientation and sequence of incorporation of nitro groups in I-VII are determined by the presence of a phenanthridone structure in them.Mono-, di-, tri-, and tetranitro-substituted I-VII were obtained and characterized.
Reaction Pathways for Arylcarbamoyl Radicals and the Cyclization of o-Substituted Phenylcarbamoyl Radicals
Leardini, Rino,Tundo, Antonio,Zanardi, Giuseppe
, p. 3164 - 3167 (2007/10/02)
N-Arylcarbamoyl radicals generated from N-arylformamides with di-t-butyl peroxide (ButOOBut) in chlorobenzene at 110 deg C give rise to a series of reactions depending on the nature and the position of the substituent in the aromatic ring.When the aryl group is phenyl or p-chlorophenyl the following reactions on carbamoyl radicals occur: (i) loss of hydrogen with formation of aryl isocyanates, whereas the loss of carbon monoxide leads to arylamines via arylaminyl radicals; (ii) dimerization to NN'-diaryloxamides; (iii) aromatic substitution on chlorobenzene leading to N-arylbenzamides (ipso-substitution) and N-arylchlorobenzamides.The isocyanates trapped by t-butyl alcohol and arylamines give t-butyl N-arylcarbamates and NN'-diarylureas.With o-substituted N-phenylformamides intramolecular cyclization is observed as well; in fact, the N-(o-cyanophenyl)formamide affords isatin via addition of the carbamoyl radical to the cyano-group while the N-formamide gives 2-benzothiazolone and phenyl radicals through an SHi reaction on the sulphur atom; finally 2-formamidobiphenyls furnish phenanthridones in very high yields.
