Substrate selective amide coupling driven by encapsulation of a coupling agent within a self-assembled hexameric capsule

2015 ◽  
Vol 51 (9) ◽  
pp. 1658-1661 ◽  
Author(s):  
Sonia Giust ◽  
Giorgio La Sorella ◽  
Laura Sperni ◽  
Giorgio Strukul ◽  
Alessandro Scarso
Keyword(s):  
Carboxylic Acids ◽  
Coupling Agent ◽  
Primary Amines ◽  
Substrate Selectivity ◽  
Synthesis Reaction ◽  
Amide Synthesis ◽  
Amide Coupling ◽  
Self Assembled

Encapsulation of a cationic carbodiimide condensing agent within a self-assembled hexameric capsule made of resorcin[4]arene units provides a nano-environment that efficiently steers the substrate selectivity in the amide synthesis reaction between carboxylic acids and primary amines.

scholarly journals Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids

2021 ◽  
pp. 174751982098715
Author(s):  
Khethobole C Sekgota ◽  
Michelle Isaacs ◽  
Heinrich C Hoppe ◽  
Ronnett Seldon ◽  
Digby F Warner ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Coupling Agent ◽  
Methyl Esters ◽  
Acid Anhydride

Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.

New diamondoid-like [Cu3B(μ-O)6] core self-assembled from Bis-Tris biobuffer for mild hydrocarboxylation of alkanes to carboxylic acids

2011 ◽  
Vol 40 (24) ◽  
pp. 6378 ◽  
Author(s):  
Alexander M. Kirillov ◽  
Yauhen Y. Karabach ◽  
Marina V. Kirillova ◽  
Matti Haukka ◽  
Armando J. L. Pombeiro
Keyword(s):  
Carboxylic Acids ◽  
Self Assembled ◽  
Core Self

Biological Activity of Novel N-Substituted Amides of endo-3- (3-Methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2- carboxylic Acid and N-Substituted Amides of 1-(5-Methylthio- 1,2,4-triazol-3-yl)cyclohexane-2-carboxylic Acids

2012 ◽  
Vol 67 (3-4) ◽  
pp. 123-128
Author(s):  
Anna Pachuta-Stec ◽  
Urszula Kosikowska ◽  
Anna Chodkowska ◽  
Monika Pitucha ◽  
Anna Malm ◽  
...  
Keyword(s):  
Biological Activity ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Condensation Reaction ◽  
Primary Amines ◽  
Pharmacological Activities

N-Substituted amides of endo-3-(3-methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene- 2-carboxylic acid and 1-(5-methylthio-1,2,4-triazol-3-yl)cyclohexane-2-carboxylic acid were prepared by the condensation reaction of endo-S-methyl-N1-(bicyclo[2.2.1]hept-5-ene-2,3- dicarbonyl)isothiosemicarbazide and S-methyl-N1-(cyclohexane-2,3-dicarbonyl)isothiosemicarbazide with primary amines. The synthesized compounds were screened for their microbiological and pharmacological activities

scholarly journals Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Zhan Li ◽  
Ke-Feng Wang ◽  
Xin Zhao ◽  
Huihui Ti ◽  
Xu-Ge Liu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Late Stage ◽  
Materials Science ◽  
Reaction Pathway ◽  
Chemical Conversion ◽  
Primary Amines ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Aliphatic Acids ◽  
Redox Active

Abstract Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky’s N-alkylpyridinium salts, respectively, alkyl carboxylic acids and primary amines serve as ideal starting materials to forge new connections. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines is disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds are efficiently constructed under simple and mild reaction conditions. The protocol is applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway.

scholarly journals Electron-Induced Modification of Self-Assembled Monolayers of Aromatic Carboxylic Acids

2020 ◽  
Vol 124 (45) ◽  
pp. 25107-25120
Author(s):  
Andika Asyuda ◽  
Rodrigo Ortiz de la Morena ◽  
Eric Sauter ◽  
Kelly Turner ◽  
Kirsty McDonald ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Self Assembled Monolayers ◽  
Aromatic Carboxylic Acids ◽  
Assembled Monolayers ◽  
Self Assembled

Self-Assembled Monolayers of Compact Phosphanes with Alkanethiolate Pendant Groups: Remarkable Reusability and Substrate Selectivity in Rh Catalysis

2008 ◽  
Vol 120 (30) ◽  
pp. 5709-5712 ◽  
Author(s):  
Kenji Hara ◽  
Ryuto Akiyama ◽  
Satoru Takakusagi ◽  
Kohei Uosaki ◽  
Toru Yoshino ◽  
...  
Keyword(s):  
Self Assembled Monolayers ◽  
Substrate Selectivity ◽  
Assembled Monolayers ◽  
Self Assembled
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