10347-11-2Relevant articles and documents
-
Pollock et al.
, p. 4390 (1968)
-
Effects of substituents on the rates of deacylation of substituted benzoyl papains. Role of a carboxylate residue in the catalytic mechanism
Zannis,Kirsch
, p. 2669 - 2674 (1978)
-
An efficient synthesis of 1,3,7-triazaspiro[4.4]nonane-2,4-dione derivatives and antimicrobial activity thereof
Krolenko, Konstantin Yu.,Silin, Olexiy V.,Vlasov, Sergiy V.,Zhuravel, Irina O.,Kovalenko, Sergiy M.
, p. 472 - 477 (2015)
Efficient methods for the synthesis of 1,3,7-triazaspiro[4.4]nonane-2,4-dione derivatives possessing an unsaturated pyrrolidine cycle have been developed affording intermediates and target compounds in high yields not requiring additional purification. Antimicrobial activity of the synthesized compounds was studied.
Practical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with N-Carbonylimidazoles
Brown, Hailee,Heller, Stephen T.,Light, Christina,Medlin, Abigail,Nelson, Hope,Richard, William
supporting information, p. 22818 - 22825 (2021/09/13)
Chemoselective transformations are a cornerstone of efficient organic synthesis; however, achieving this goal for even simple transformations, such as acylation reactions, is often a challenge. We report that N-carbonylimidazoles enable catalytic chemodivergent aniline or alcohol acylation in the presence of pyridinium ions or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), respectively. Both acylation reactions display high and broad chemoselectivity for the target group. Unprecedented levels of chemoselectivity were observed in the DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N?H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation of the acylimidazole electrophile.
Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids
Betori, Rick C.,Davies, Anna V.,Fitzpatrick, Keegan P.,Scheidt, Karl A.
supporting information, p. 9143 - 9148 (2020/03/30)
As a key element in the construction of complex organic scaffolds, the formation of C?C bonds remains a challenge in the field of synthetic organic chemistry. Recent advancements in single-electron chemistry have enabled new methods for the formation of various C?C bonds. Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium in situ followed by a radical–radical coupling was made possible merging N-heterocyclic carbene (NHC) and photoredox catalysis. The utility of this protocol in synthesis was showcased in the late-stage functionalization of a variety of pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing the advantages of this protocol over alternative methodologies.
