70786-03-7Relevant academic research and scientific papers
N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst
Dindarloo Inaloo, Iman,Majnooni, Sahar,Eslahi, Hassan,Esmaeilpour, Mohsen
, p. 13266 - 13278 (2020/10/07)
An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is
Microwave promoted reaction of purin-6-yl magnesium halides with aldehydes in dichloromethane at 100u202f°C
Gordon, Malcolm R.,Lindell, Stephen D.
, p. 1945 - 1947 (2018/04/16)
Treatment of a dichloromethane solution of 9-benzyl or 9-phenyl 6-iodopurine with ethereal ethylmagnesium bromide at ambient temperature gives the corresponding purin-6-yl magnesium halides. Addition of an aldehyde followed by heating at 100 °C in a microwave reactor yielded the corresponding carbinols in 52–81% yield.
Direct N9-arylation of purines with aryl halides
Larsen, Anders Foller,Ulven, Trond
supporting information, p. 4997 - 4999 (2014/05/06)
An efficient method for N-arylation of purines is reported. The N-arylation is catalysed by Cu(i) and 4,7-bis(2-hydroxyethylamino)-1,10-phenanthroline (BHPhen) in aqueous DMF or ethanol. The reaction generally proceeds with high selectivity for the N
Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles
Antilla, Jon C.,Baskin, Jeremy M.,Barder, Timothy E.,Buchwald, Stephen L.
, p. 5578 - 5587 (2007/10/03)
This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein.
Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
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, (2015/03/06)
The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.
Purines. VIII. Reactions of 1-Benzoyl-1,6-dihydro-9-phenyl-9H-purine-6-carbonitrile (9-Phenylpurine Reissert Compound) with Acid, Bases, and Electrophiles
Tanji, Ken-ichi,Sato, Susumu,Miyashita, Akira,Oishi, Etsuo,Higashino, Takeo
, p. 187 - 189 (2007/10/02)
1-Benzoyl-1,6-dihydro-9-phenyl-9H-purine-6-carbonitrile (1, 9-phenylpurine Reissert compound) was hydrolyzed in an acid medium to give the ring fission product of the pyrimidine ring (3, 4).Alkaline hydrolysis of 1 gave 9-phenyl-9H-purine (2) and benzoic acid (5).The anion of 1 generated from 1 and sodium hydride in tetrahydrofuran underwent aromatization, resulting in the formation of 9-phenyl-9H-purine-6-carbonitrile (6) together with 2.The reaction of 1 with aromatic aldehydes in the presence of sodium hydride proceeded to give the 6-purinylmethyl benzoates (8a-c), together with 2 and 9.On the other hand, the reaction of 1 with 2,4-dinitrochlorobenzene in the presence of sodium hydride failed to give the corresponding 6-arylpurine, and the aromatization product 6 was obtained.Keywords - 9H-purine; Reissert compound anion; 9H-purin-6-ylmethyl benzoate
