203321-89-5Relevant academic research and scientific papers
Efficient and expeditious chemoselective BOC protection of amines in catalyst and solvent-free media
Viswanadham, Balaga,Mahomed, Abdul S.,Friedrich, Holger B.,Singh, Sooboo
, p. 1355 - 1363 (2017/02/15)
A green and eco-friendly route for the almost quantitative BOC protection of a large variety of aliphatic and aromatic amines, amino acids, and amino alcohols is reported in catalyst and solvent-free media under mild reaction conditions. The products were confirmed by 1H, 13C NMR, IR spectroscopy, and in some cases, elemental analysis. This protocol does not require any water quenches, solvent separations, and purification steps, such as recrystallization and column chromatography.
Pd(II)/Ag(I)-Promoted One-Pot Synthesis of Cyclic Ureas from (Hetero)Aromatic Amines and Isocyanates
Youn, So Won,Kim, Yi Hyun
supporting information, p. 6140 - 6143 (2016/12/09)
A simple and facile one-pot reaction has been developed to afford a diverse range of N,N′-disubstituted benzimidazolones and imidazopyridinones containing two differently substituted N atoms. A cooperative Pd(II)/Ag(I) system promotes the sequential addition/intramolecular C-H amidation reaction of (hetero)aromatic amines and isocyanates, leading to the formation of two C-N bonds. A mechanism involving radical intermediates generated by single-electron transfer (SET) in the presence of a Ag2CO3 oxidant and Pd(OAc)2 Lewis acid is proposed. This protocol offers an operationally easy, simple, and robust approach with the use of readily available starting materials, good functional group tolerance, and high efficiency.
Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates
Lim, Diane S. W.,Lew, Tedrick T. S.,Zhang, Yugen
supporting information, p. 6054 - 6057 (2016/01/09)
N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.
Copper(i)-catalyzed amidation reaction of organoboronic esters and isocyanates
Salim Lew, Tedrick Thomas,Wen Lim, Diane Shu,Zhang, Yugen
, p. 5140 - 5143 (2015/12/05)
A simple and efficient methodology for the preparation of amides from easily available organoboronic esters and isocyanates has been accomplished using a ligand-free copper(i) catalyst. The reaction system demonstrated a broad substrate scope and provided convenient access to a wide variety of secondary amides.
Synthesis of indolines, indoles, and benzopyrrolizidinones from simple aryl azides
Brucelle, Fran?ois,Renaud, Philippe
supporting information; experimental part, p. 3048 - 3051 (2012/08/14)
A simple approach to prepare indolines and benzopyrrolizidinones from ortho-azidoallylbenzenes via a tandem radical addition/cyclization is described. The use of triethylborane to initiate and sustain the process provides the best results. Indolines are easily converted into the corresponding indoles by oxidation with manganese dioxide.
Curtius rearrangement of aromatic carboxylic acids to access protected anilines and aromatic ureas
Lebel, Helene,Leogane, Olivier
, p. 5717 - 5720 (2007/10/03)
(Diagram presented) The reaction of a chloroformate or di-tert-butyl dicarbonate and sodium azide with an aromatic carboxylic acid produces the corresponding acyl azide, presumably through the formation of an azidoformate. The acyl azide undergoes a Curtius rearrangement to form an isocyanate derivative which is trapped either by an alkoxide or by an amine to form the aromatic carbamate or urea. The reaction conditions are compatible with a variety of functional groups and allow the synthesis of a number of aniline derivatives containing alkyl, halide, nitro, ketone, ether, and thioether substituents.
Fluorine-containing 1,4-disubstituted piperidine derivatives
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, (2008/06/13)
Novel fluorine-containing 1,4-disubstituted piperidine derivatives, represented by general formula ?I! STR1 such as, for example, (2R)-N-?1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl!-2-?(1R)-3,3-difluorocyclopentyl!-2-hydroxy-2-phenylacetamide or pharmaceutically acceptable salt thereof, are potent and selective antagonists for muscarinic M3 receptors with little side effects. The compounds of formula ?I! exhibit excellent oral activity, duration of activity and pharmacolkinetics. They are useful for treatment and prophylaxis of respiratory diseases, such as chronic obstructive pulmonary diseases; urinary diseases, such as urinary incontinence; and digestive diseases, such as irritable bowel syndrome, and motion sickness.
