Thioacylation reactions for the surface functionalization of phosphorus-containing dendrimers.

Org Lett

Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France.

Published: April 2004

The functionalization of phosphorus-containing dendrimers was easily achieved through thioacylation reactions involving new dendrimers capped with dithioester end groups and various functionalized amines. These reactions were successfully applied to the first generation (12 end groups) and the third generation of the dendrimer (48 end groups) and allowed their functionalization by various primary or secondary amines, alcohols, glycols, and azides. [reaction: see text]

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol049720rDOI Listing

Publication Analysis

Top Keywords

thioacylation reactions
8
functionalization phosphorus-containing
8
phosphorus-containing dendrimers
8
reactions surface
4
surface functionalization
4
dendrimers functionalization
4
dendrimers easily
4
easily achieved
4
achieved thioacylation
4
reactions involving
4

Similar Publications

Photoinduced Decarboxylative Thioacylation of N-Hydroxyphthalimide Esters with Tetraalkylthiuram Disulfides.

Chemistry

December 2024

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, People's Republic of China.

Dithiocarbamate is a key structural sequence in pharmaceuticals and agrochemicals, and its synthesis is crucial in organic chemistry. Although significant progress has been made in related synthesis research, developing a practical and universal synthesis method remains fascinating. Herein, we report a new visible-light-induced decarboxylation coupling reaction between N-hydroxyphthalimide esters and tetraalkylthiuram disulfides, which uses Ir(ppy) as a photocatalyst to promote the generation of corresponding decarboxylation thioacylation product-dithiocarbamates in high yields.

View Article and Find Full Text PDF

Chemoselective Thioacylation of Amines Enabled by Synergistic Defluorinative Coupling.

Org Lett

August 2024

School of Chemistry and Chemical Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, South China University of Technology, Guangzhou 510640, China.

A mild and chemoselective method for the thioacylation of amines, including amino acids and peptides, using -difluoroalkenes and sulfide, is reported. The distinguishing of the different nucleophilic sites (-site and diverse -sites) by the chemoselective C-F bond functionalization of -difluoroalkenes enables the unique synergistic defluorinative coupling reaction. This reaction features mild conditions, is operationally simple, efficient, and gram-scalable, tolerates various functional groups, and is activator-free and without racemization.

View Article and Find Full Text PDF

Synthesis of Complex Thiazoline-Containing Peptides by Cyclodesulfhydration of N-Thioacyl-2-Mercaptoethylamine Derivatives.

Angew Chem Int Ed Engl

June 2023

Department of Enzymology, Institute of Biochemistry and Biotechnology, Martin Luther University Halle-Wittenberg, Charles Tanford Protein Center, Kurt-Mothes-Str. 3a, 06120, Halle (Saale), Germany.

Herein we report a mild, efficient, and epimerization-free method for the synthesis of peptide-derived 2-thiazolines and 5,6-dihydro-4H-1,3-thiazines based on a cyclodesulfhydration of N-thioacyl-2-mercaptoethylamine or N-thioacyl-3-mercaptopropylamine derivatives. The described reaction can be easily carried out in aqueous solutions at room temperature and it is triggered by change of the pH, leading to complex thiazoline or dihydrothiazine derivatives without epimerization in excellent to quantitative yields. The new method was applied in the total synthesis of the marine metabolite mollamide F, resulting in the revision of its stereochemistry.

View Article and Find Full Text PDF
Article Synopsis
  • Researchers are making progress in developing new small molecules that can assist in organocatalyzed thioacyl aminolysis, which is a type of chemical reaction.
  • They have successfully synthesized a unique compound based on tetrahydroisoquinoline that includes both thiol and iminium groups, enabling crucial chemical reactions like transthioesterification and amine capture.
  • The study highlights their findings on the effectiveness of the new organocatalyst and outlines potential future improvements to enhance its use in chemical processes that don't rely on cysteine.
View Article and Find Full Text PDF

A new series of N-thioacylated ciprofloxacin 3a-n were designed and synthesized based on Willgerodt-Kindler reaction. The results of in vitro urease inhibitory assay indicated that almost all the synthesized compounds 3a-n (IC = 2.05 ± 0.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!