98%
921
2 minutes
20
In this study, we developed a new addition reaction of chlorosulfonyl isocyanate (CSI), starting from 2-ethyl-3a,4,7,7a-tetrahydro-1-isoindole-1,3(2)-dione. The addition reaction of CSI with 2-ethyl-3a,4,7,7a-tetrahydro-1-isoindole-1,3(2)-dione resulted in the formation of ylidenesulfamoyl chloride, whose exact configuration was determined by X-ray crystal analysis. We explain the mechanism of product formation supported by theoretical calculations.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6541324 | PMC |
http://dx.doi.org/10.3762/bjoc.15.89 | DOI Listing |
J Biochem Mol Toxicol
April 2025
Department of Chemistry, Faculty of Sciences, Atatürk University, Erzurum, Turkey.
An efficient one-pot method has been developed for synthesizing novel isoindolinone derivatives from 2-benzoylbenzoic acid using chlorosulfonyl isocyanate and alcohols. This reaction occurs under mild, metal-free conditions, rendering it a sustainable and effective approach for isoindolinone synthesis. The inhibitory potential of the synthesized compounds against human carbonic anhydrase (hCA) I and II isozymes was evaluated and compared with the standard inhibitor, acetazolamide (AAZ).
View Article and Find Full Text PDFJ Org Chem
November 2024
Department of Chemistry and Biochemistry, Baylor University, One Bear Place #97348, Waco, Texas 76798-7348, United States.
Chlorosulfonyl isocyanate (CSI) is a complex reagent capable of facilitating numerous synthetic transformations, including lactam/lactone formation, sulfonylation, Friedel-Crafts-type acylations, and cycloadditions. Annulation reactions to form nitrogen-, oxygen-, and sulfur-bearing heterocycles have been observed with CSI; however, the application of CSI toward the generation of fused cyclic ketone ring systems has not been previously reported. A serendipitous discovery of the pertinence of CSI occurred during a structure-activity relationship campaign around our established lead benzosuberene-based molecule that functions as a potent inhibitor of tubulin polymerization.
View Article and Find Full Text PDFJ Biochem Mol Toxicol
September 2024
Department of Chemistry, Faculty of Sciences, Atatürk University, Erzurum, Turkey.
Synthesis of novel unnatural amino acids (UAAs) from 4-oxo-4-phenylbut-2-enoic acid derivatives with intramolecular aza-Michael addition reaction in the presence of chlorosulfonyl isocyanate (CSI) was reported in soft conditions without any metal catalyst. Acids and base as a catalyst, and solvents effects were investigated for the synthesis of novel UAAs. This novel method provides inexpensive, practicable, and efficient approach to generate UAAs.
View Article and Find Full Text PDFFuture Med Chem
June 2024
Department of Chemistry, Faculty of Sciences, Atatürk University, Erzurum, 25240, Turkey.
A highly efficient one-step method has been developed for the synthesis of benzofuranyl derivatives from 2-benzoylcyclohexane-1-carboxylic acid derivatives using chlorosulfonyl isocyanate. This novel method provides a practical, cost-effective and efficient approach. The inhibitory effects of benzofuranyl derivatives on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes were investigated.
View Article and Find Full Text PDFTalanta
February 2024
Selcuk University, Department of Chemistry, 42075, Konya, Turkey. Electronic address:
UiO-66-NH material is a variant of Zr-based MOF most widely used for various applications, exhibiting unprecedented excellent hydrothermal and physicochemical stability. In this study, after UiO-66-NH reacted with chlorosulfonyl isocyanate, the fluorescent UiO-66-NG probe was prepared by interacting with the N-methylglucamine molecule. The structure of the prepared probe was confirmed by characterizing them with techniques such as FTIR, SEM, and XRD.
View Article and Find Full Text PDF