305806-99-9Relevant academic research and scientific papers
Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis
Lee, Hyo-Jun,Huang, Xiao,Sakaki, Shigeyoshi,Maruoka, Keiji
, p. 848 - 855 (2021/02/09)
A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.
One-Pot Synthesis of α-Branched N-Acylamines via Titanium-Mediated Condensation of Amides, Aldehydes, and Organometallics
Dai, Chunhui,Genovino, Julien,Bechle, Bruce M.,Corbett, Matthew S.,Huh, Chan Woo,Rose, Colin R.,Sun, Jianmin,Warmus, Joseph S.,Blakemore, David C.
supporting information, p. 1064 - 1067 (2017/03/15)
A three-component, titanium-mediated synthesis of α-branched N-acylamines from commercial or readily accessible amides, aldehydes, and organometallic reagents is reported. The transformation proceeds under mild reaction conditions and tolerates a variety of functional groups (including nitrile, carbamate, olefin, basic amine, furan, and other sensitive heteroaromatics) to generate a large umbrella of α-branched N-acylamine products in high yields. The operationally practical procedure enables the use of this method in parallel chemical synthesis, a valuable feature that can facilitate the screening of bioactive molecules by medicinal chemists.
An Unconventional Reaction of 2,2-Diazido Acylacetates with Amines
H?ring, Andreas P.,Biallas, Phillip,Kirsch, Stefan F.
supporting information, p. 1526 - 1539 (2017/04/01)
We have discovered that 2,2-diazido acylacetates, a class of compounds with essentially unknown reactivity, can be coupled to amines through a new strategy that does not involve any reagents. 2,2-Diazido acetate is the unconventional leaving group under carbon–carbon bond cleavage. This reaction leads to the construction of amide bonds, tolerates various functionalities and is performed equally well in numerous solvents under experimentally simple conditions. We also demonstrate that the isolation of the 2,2-diazido acylacetate compounds can be circumvented: Acylacetates were easily fragmented when treated with (Bu4N)N3 and iodine in the presence of an amine at room temperature. By using this method, a broad range of acylacetates with various structural motifs were directly transformed into amides.
Method for preparing some 1-adamantancecarboxamides
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Page column 4, (2010/01/30)
This invention relates to a method for the novel preparation of 1-adamantanecarboxamides and 1-adamantaneacetamides. Adamantanecarboxamides and adamantaneacetamides are prepared in high yields (80-100%) by treating adamantanecarboxylic acid and adamantaneacetic acid with N,N-diethyl-1,1,2,3,3,3-hexafluoropropylamine, followed by addition of aqueous ammonia or the appropriate amine. The procedure, carried out at ambient temperature using common laboratory equipment, is both convenient and rapid, requiring no more than one or two hours. Several reactions can be carried out simultaneously.
