2621-80-9Relevant articles and documents
Synthesis of 4-substituted-1,2-dihydroquinolines by means of gold-catalyzed intramolecular hydroarylation reaction of n-ethoxycarbonyl-n-propargylanilines
Arcadi, Antonio,Calcaterra, Andrea,Fabrizi, Giancarlo,Fochetti, Andrea,Goggiamani, Antonella,Iazzetti, Antonia,Marrone, Federico,Marsicano, Vincenzo,Mazzoccanti, Giulia,Serraiocco, Andrea
supporting information, (2021/06/21)
An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-Npropargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-metasubstituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning.
Synthesis of Acetaminophen Analogues Containing α-Amino Acids and Fatty Acids for Inhibiting Hepatotoxicity
Imai, Nobuyuki,Jung, Seunghee,Kawashima, Yuya,Noguchi, Takuya
, p. 3686 - 3696 (2019/09/30)
Acetaminophen is a popular antipyretic analgesic medicine that has weaker anti-inflammatory properties and lower incidence of side effects than nonsteroidal anti-inflammatory drugs (NSAIDs). However, acetaminophen causes hepatotoxicity due to the reactive metabolite N -acetyl- p -benzoquinone imine (NAPQI). We have obtained acetaminophen analogues in 57-99percent yields by using aniline derivatives with protected α-amino acids and fatty acids via the corresponding mixed carbonic carboxylic anhydrides in aqueous MeCN. We have also succeeded in synthesizing AM404 analogues in 76-97percent yields, which are expected to be promising candidates for reducing hepatotoxicity.
Teaching Old Compounds New Tricks: DDQ-Photocatalyzed C?H Amination of Arenes with Carbamates, Urea, and N-Heterocycles
Das, Somnath,Natarajan, Palani,K?nig, Burkhard
supporting information, p. 18161 - 18165 (2017/12/28)
The C?H amination of benzene derivatives was achieved using DDQ as photocatalyst and BocNH2 as the amine source under aerobic conditions and visible light irradiation. Electron-deficient and electron-rich benzenes react as substrates with moderate to good product yields. The amine scope of the reaction comprises Boc-amine, carbamates, pyrazoles, sulfonimides and urea. Preliminary mechanistic investigations indicate arene oxidation by the triplet of DDQ to radical cations with different electrophilicity and a charge transfer complex between the amine and DDQ as intermediate of the reaction.
BMIm HCO3: an ionic liquid with carboxylating properties. Synthesis of carbamate esters from amines
Di Nicola,Arcadi,Rossi
supporting information, p. 9895 - 9898 (2016/12/07)
1-Butyl-3-methylimidazolium hydrogen carbonate (BMIm HCO3) was used as an ionic liquid with carboxylating properties able to convert, in the presence of an alkyl halide, amines into the corresponding carbamate esters. Moderate to good yields of
One-pot preparation of carbamoyl benzotriazoles and their applications in the preparation of ureas, hydrazinecarboxamides and carbamic esters
Mao, Hui,Liu, Huili,Tu, Yawei,Zhong, Zhiyun,Lv, Xin,Wang, Xiaoxia
, p. 13 - 22 (2016/02/18)
Carbamoyl benzotriazoles were conveniently synthesized in one-pot from carboxylic acids, diphenyl phosphorazidate (DPPA) and 1H-benzotriazole (BtH). The reactivity and applications of carbamoyl benzotriazoles were also explored. Carbamoyl benzotriazoles react smoothly with amino acids, hydrazines and alcohols, thus providing facile access to the corresponding ureas, hydrazinecarboxamides and carbamic esters, respectively, in good to excellent yields.
Convenient synthesis of acetaminophen analogues containing α-amino acids and fatty acids via their mixed carbonic carboxylic anhydrides in aqueous organic solvent
Jung, Seunghee,Tsukuda, Yuki,Kawashima, Rie,Ishiki, Takumi,Matsumoto, Ayaka,Nakaniwa, Aya,Takagi, Miho,Noguchi, Takuya,Imai, Nobuyuki
, p. 5718 - 5720 (2013/09/24)
Acetaminophen analogues containing α-amino acid and fatty acids were easily synthesized in 77-99% yields from the corresponding mixed carbonic carboxylic anhydrides of α-amino acid and fatty acids using aniline derivatives in aqueous MeCN.
Reaction of organozinc halides with aryl isocyanates
Yang, Haoran,Huang, Danfeng,Wang, Ke-Hu,Xu, Changming,Niu, Teng,Hu, Yulai
supporting information, p. 2588 - 2593 (2013/03/28)
Reformatsky reagent, benzylzinc bromide or alkylzinc iodides react with aryl isocyanates directly to give corresponding N-substituted carbamates under mild reaction conditions. However, the reaction of allylzinc bromide or propargylzinc bromide with aryl isocyanates produces the corresponding N-substituted amides. The reactions provide alternative methods for the synthesis of N-substituted carbamates or amides.
Design and synthesis of novel stiripentol analogues as potential anticonvulsants
Aboul-Enein, Mohamed N.,El-Azzouny, Aida A.,Attia, Mohamed I.,Maklad, Yousreya A.,Amin, Kamilia M.,Abdel-Rehim, Mohamed,El-Behairy, Mohammed F.
experimental part, p. 360 - 369 (2012/03/11)
A series of stiripentol (STP) analogues namely, 2-[(1E)-1-(1,3-benzodioxol- 5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(aryl/H)hydrazinecarboxamides 7a-h, (±)-(5RS)-N-(aryl/H)-(1,3-benzodioxol-5-yl)-3-tert-butyl-4, 5-dihydro-1H-pyrazole-1-carboxamides (±)-8a-h, and (±)-[(5RS)-(1, 3-benzodioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](aryl)methanones (±)-13a-f was synthesized by adopting appropriate synthetic routes and was pharmacologically evaluated in the preliminary anticonvulsant screens. The selected bioactive new chemical entities were subjected to ED50 determination and neurotoxicity evaluation. The most active congeners are 7h in MES screen and (±)-13b in scPTZ screen which displayed ED50 values of 87 and 110 mg/kg, respectively, as compared to that of STP (ED 50 = 277.7 and 115 mg/kg in MES and scPTZ, respectively).
Synthesis of aryl carbamates via copper-catalyzed coupling of aryl halides with potassium cyanate
Yang, Xinye,Zhang, Yihua,Ma, Dawei
supporting information, p. 2443 - 2446,4 (2020/08/31)
Coupling of aryl halides with potassium cyanate takes place at 100-110 °C in alcohols under the catalysis of CuI (cuprous iodide) and 2-(2,6-dimethylphenylamino)-2-oxoacetic acid, affording the corresponding aryl carbamates with great diversity. Copyright
Copper-catalyzed coupling of arylboronic acids with potassium cyanate: A new approach to the synthesis of aryl carbamates
Kianmehr, Ebrahim,Baghersad, Mohammad Hadi
supporting information; experimental part, p. 2599 - 2603 (2011/11/29)
The copper-catalyzed coupling of aromatic boronic acids with potassium cyanate in the presence of an alcohol has been employed for the synthesis of arylcarbamates. This simple and highly efficient approach can be carried out in air at room temperature and, importantly, no base, ligand, or additive is required. Copyright
