7451-55-0Relevant academic research and scientific papers
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.
Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement
Kumar, Arun,Kumar, Naveen,Sharma, Ritika,Bhargava, Gaurav,Mahajan, Dinesh
, p. 11323 - 11334 (2019/09/10)
Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.
Chemoselective synthesis of carbamates using CO2 as carbon source
Riemer, Daniel,Hirapara, Pradipbhai,Das, Shoubhik
, p. 1916 - 1920 (2018/08/17)
Synthesis of carbamates directly from amines using CO2 as the carbon source is a straightforward and sustainable approach. Herein, we describe a highly effective and chemoselective methodology for the synthesis of carbamates at room temperature and atmosp
Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis
Isley, Nicholas A.,Dobarco, Sebastian,Lipshutz, Bruce H.
supporting information, p. 1480 - 1488 (2014/03/21)
A single set of conditions consisting of a palladium catalyst, a commercially available ligand, and a base, allow for several types of C-N bond constructions to be conducted in water with the aid of a commercially available "designer" surfactant (TPGS-750-M). Products containing a protected NH2 group in the form of a carbamate, sulfonamide, or urea can be fashioned starting with aryl or heteroaryl bromides, iodides, and in some cases, chlorides, as substrates. Reaction temperatures are in the range of room temperature to, at most, 50 °C, and result in essentially full conversion and good isolated yields.
PdCl2 catalyzed efficient assembly of organic azides, CO, and alcohols under mild conditions: A direct approach to synthesize carbamates
Ren, Long,Jiao, Ning
, p. 3706 - 3709 (2014/04/03)
A simple and readily available PdCl2 catalyzed carbamate synthesis method via isocyanate generation and application in situ has been developed. This chemistry provides an efficient and practical approach to synthesize carbamates from simple organic azides, CO atmosphere and alcohols. The broad scope, mild and neutral conditions, and only N2 as the byproduct make this transformation very useful. Moreover, simple examples of modification of bioactive molecules and construction of macrocycles were achieved through this protocol. This journal is the Partner Organisations 2014.
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.
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
1,7-palladium migration via C-H activation, followed by intramolecular amination: Regioselective synthesis of benzotriazoles
Zhou, Jun,He, Jianjun,Wang, Binjie,Yang, Weijun,Ren, Hongjun
supporting information; experimental part, p. 6868 - 6870 (2011/06/21)
A novel 1,7-palladiummigration-cyclization-dealkylation sequence for the regioselective synthesis of benzotriazoles has been developed. These reactions proceed in excellent yields with high regioselectivities. The mechanism of the reaction has also been investigated.
Synthesis and antibacterial activity of isothiazolyl oxazolidinones and analogous 3(2H)-isothiazolones
Adibpour, Neda,Khalaj, Ali,Rajabalian, Saeed
scheme or table, p. 19 - 24 (2010/03/24)
The synthesis and antibacterial activity of several new 5-((3-oxoisothiazol-2(3H)-yl)methyl)-3-phenyloxazolidin-2-ones 8 and analogous 2-(4-substituted phenyl)-3(2H)-isothiazolones 3 and 4 substituted at 4 and/or 3-positions of the phenyl moiety with different groups of which some have shown to increase the antibacterial activity of both 3-aryl-2-oxazolidinones and 3(2H)-isothiazolones is described. The most active compounds were isothiazolyl oxazolidinones 8a,j with unsubstituted and 8b with 4-F substituted phenyl rings which showed activities higher than analogous 3(2H)-isothiazolones and comparable or superior to linezolid, vancomycin, and ciprofloxacin against some tested microorganisms. The change in position of F and/or the use of larger substituents gave compounds with reduced or no activity. Evaluation of cytotoxicity to mouse fibroblast (NIH/3T3) cells indicated that these compounds exhibit antibacterial activity at non-cytotoxic concentrations.
Synthesis of carbamates from diethoxycarbonyl hydrazine derivatives by E1cB eliminative cleavage of the N-N′-bond rather than reduction
Magnus, Philip,Garizi, Negar,Seibert, Kimberly A.,Ornholt, Alexandra
supporting information; experimental part, p. 5646 - 5648 (2010/02/28)
[Chemical Equation Presented] Treatment of diethoxycarbonyl hydrazine derivatives with methyl bromoacetate/Cs2CO3/MeCN at 50°C followed by heating to 80°C resulted in N-N′ bond cleavage to the corresponding carbamates.
