85221-16-5Relevant academic research and scientific papers
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.
METHOD FOR PRODUCING CARBAMATE
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Paragraph 0049, (2018/10/16)
PROBLEM TO BE SOLVED: To provide a method for producing carbamate in which a high yield can be obtained and the amount of by-products produced can be reduced. SOLUTION: In the method, carbamate is synthesized using at least one member selected from the group consisting of amine and derivative thereof, alcohol having 3 or more carbon atoms and carbon dioxide as a raw material, cerium oxide as a catalyst, and 2-cyanopyridine as a dehydrating agent. By using an alcohol having 3 or more carbon atoms, a high yield can be obtained and the amount of by-products produced can be reduced. In addition, the pressure of carbon dioxide can be lowered and the production can be of ease. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPO&INPIT
Copper-catalyzed carbonylation of anilines by diisopropyl azodicarboxylate for the synthesis of carbamates
Usman, Muhammad,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 107542 - 107546 (2016/11/29)
A Cu-catalyzed efficient methodology for the direct carbonylation of anilines has been developed. The N-H bond cleavage and N-C bond formation were notably achieved under solvent-free conditions and a variety of carbamates were synthesized from readily available anilines using diisopropyl azodicarboxylate (DIAD) as the carbonylating source.
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.
N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement
Yoganathan, Sabesan,Miller, Scott J.
supporting information, p. 602 - 605 (2013/04/11)
An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.
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
Reversible double insertion of aryl isocyanates into the Ti-O bond of titanium(IV) isopropoxide
Ghosh, Rajshekhar,Nethaji, Munirathinam,Samuelson, Ashoka G.
, p. 1282 - 1293 (2007/10/03)
The insertion of phenyl isocyanate into titanium isopropoxide leads to the formation of a dimeric complex [Ti(OiPr)2(μ-O iPr){C6H5N(OiPr)CO}]2 (1) which has been structurally characterized. Reaction of titanium isopropoxide with two and more than 2 equiv. of phenyl isocyanate is complicated by competitive, reversible insertion between the titanium carbamate and titanium isopropoxide. The ligand formed by insertion of phenyl isocyanate into the titanium carbamate has been structurally characterized in its protonated form C6H5N{C(OiPr)O}C(O)N(H)C6H 5 (3aH). Insertion into the carbamate is kinetically favored whereas insertion into isopropoxide gives the thermodynamically favored product.
THE REACTION OF IMIDOYL RADICALS WITH MULTIPLE CARBON-CARBON BONDS
Leardini, Rino,Nanni, Daniele,Tundo, Antonio,Zanardi, Giuseppe
, p. 637 - 642 (2007/10/02)
A general view on the reaction between imidoyl radicals and carbon-carbon double or triple bonds is given; the synthesis of substituted quinolines starting from imines and alkenes is described, pointing out the differences with respect to the analogous reaction performed with alkynes.
Homolytic Annulation by Reaction of Imidoyl Radicals with Diethyl Azodicarboxylate: a New Route to Nitrogen Heterocycle Derivatives
Leardini, Rino,Nanni, Daniele,Tundo, Antonio,Zanardi, Giuseppe
, p. 757 - 758 (2007/10/02)
An easily effected aromatic annulation is described, involving the reaction of arylimidoyl radicals with diethyl azodicarboxylate to give 1,2-dihydro-1,2-diethoxycarbonyl-benzo- and -pyrido-1,2,4-triazines.
