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Ranunculin, Protoanemonin, and Anemonin: Pharmacological and Chemical Perspectives.
Curr Med Chem
February 2024
Department of Biomedical and Pharmaceutical Sciences, L. S. Skaggs College of Pharmacy, Kasiska Division of Health Sciences, Idaho State University, Pocatello, ID, 83209, USA.
Ranunculin, a glucoside, serves as a chemotaxonomic marker in Ranunculaceae plants. When these plants are damaged, an enzyme β-glucosidase triggers the conversion of ranunculin into protoanemonin through hydrolysis. Subsequently, protoanemonin undergoes cyclodimerization to form anemonin.
View Article and Find Full Text PDFTriethylamine-Promoted Oxidative Cyclodimerization of 2-Azirine-2-carboxylates to Pyrimidine-4,6-dicarboxylates: Experimental and DFT Study.
Molecules
May 2023
Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya Nab., 199034 St. Petersburg, Russia.
An unprecedented oxidative cyclodimerization reaction of 2-azirine-2-carboxylates to pyrimidine-4,6-dicarboxylates under heating with triethylamine in air is described. In this reaction, one azirine molecule undergoes formal cleavage across the C-C bond and another across the C=N bond. According to the experimental study and DFT calculations, the key steps of the reaction mechanism include nucleophilic addition of ,-diethylhydroxylamine to an azirine to form an (aminooxy)aziridine, generation of an azomethine ylide, and its 1,3-dipolar cycloaddition to the second azirine molecule.
View Article and Find Full Text PDFDivergent cyclodimerizations of styrylnaphthols under aerobic visible-light irradiation and Brønsted acid catalysis.
Org Biomol Chem
December 2022
Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
Dimeric cyclization reactions show great potential to rapidly form highly substituted complex cyclic molecules from simple starting materials. However, such an appealing process is often hampered by the lack of selectivity. Herein we report two divergent cyclodimerization reactions of 1-styrylnaphthalen-2-ol derivatives under simple and very mild reaction conditions.
View Article and Find Full Text PDFFirst example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell.
Beilstein J Org Chem
August 2022
Department of Scienze di Base e Applicate per l'Ingegneria, Sapienza University, via del Castro Laurenziano, 7, 00161, Rome, Italy.
In this paper we present the first electrochemical generation of NHC carried out in a divided flow cell. The flow cell operated in the recycle mode. The need for a divided cell derived from the anodic electroactivity of the electrogenerated carbene.
View Article and Find Full Text PDFComplexity of imine and amine Schiff-base tin(II) complexes: drastic differences of amino and pyridyl side arms.
Dalton Trans
January 2022
Department of Materials Science and Engineering, School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology (VISTEC), Wangchan, Rayong 21210, Thailand.
A series of homoleptic and heteroleptic imine and amine Schiff-base tin(II) complexes containing dimethylamino and pyridyl side arms were synthesized and structurally characterized. While the tin complexes containing the dimethylamino side arm could be prepared in good yield, unusual cyclodimerization and ligand dimerization were observed for the first time for Schiff-base tin complexes having a pyridyl side arm due to the added stabilization offered by the pyridyl ring. The amine Schiff-base tin(II) complexes were active for the ring-opening copolymerization of succinic anhydride (SA) and cyclohexene oxide (CHO) at 110 °C giving highly alternating poly(SA--CHO).
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