A novel and practical approach to access saturated ketones from unsaturated ketone derivatives via a CS/BuOK system in dimethyl sulfoxide (DMSO) is reported. The generation of xanthate salt through the reaction of carbon disulfide and potassium -butoxide is essential to this transformation. Deuterium-labeling experiments demonstrated that DMSO can act as a hydrogen donor.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.3c00903 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Chemoselective Reduction of α,β-Unsaturated Carbonyl Compounds via a CS/BuOK System: Dimethyl Sulfoxide as a Hydrogen Source.
J Org Chem
August 2023
Peptide Chemistry Research Institute, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran 19697-64499, Iran.
A novel and practical approach to access saturated ketones from unsaturated ketone derivatives via a CS/BuOK system in dimethyl sulfoxide (DMSO) is reported. The generation of xanthate salt through the reaction of carbon disulfide and potassium -butoxide is essential to this transformation. Deuterium-labeling experiments demonstrated that DMSO can act as a hydrogen donor.
View Article and Find Full Text PDFUnexpected Decarbonylation of Acylethynylpyrroles under the Action of Cyanomethyl Carbanion: A Robust Access to Ethynylpyrroles.
Molecules
February 2023
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Science, 664033 Irkutsk, Russia.
It has been found that the addition of CHCN anion to the carbonyl group of acylethynylpyrroles, generated from acetonitrile and -BuOK, results in the formation of acetylenic alcohols, which undergo unexpectedly easy (room temperature) decomposition to ethynylpyrroles and cyanomethylphenylketones (-Favorsky reaction). This finding allows a robust synthesis of ethynylpyrroles in up to 95% yields to be developed. Since acylethynylpyrroles became available, the strategy thus found makes ethynylpyrroles more accessible than earlier.
View Article and Find Full Text PDF-Phenacyldibromobenzimidazoles-Synthesis Optimization and Evaluation of Their Cytotoxic Activity.
Molecules
July 2022
Faculty of Chemistry, Warsaw University of Technology, Noakowskiego St. 3, 00-664 Warsaw, Poland.
Antifungal -phenacyl derivatives of 4,6- and 5,6-dibromobenzimidazoles are interesting substrates in the synthesis of new antimycotics. Unfortunately, their application is limited by the low synthesis yields and time-consuming separation procedure. In this paper, we present the optimization of the synthesis conditions and purification methods of -phenacyldibromobenzimidazoles.
View Article and Find Full Text PDFSynthesis of dihydrotestosterone derivatives modified in the A-ring with (hetero)arylidene, pyrazolo[1,5-a]pyrimidine and triazolo[1,5-a]pyrimidine moieties and their targeting of the androgen receptor in prostate cancer.
J Steroid Biochem Mol Biol
July 2021
Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary. Electronic address:
One of the main directions of steroid research is the preparation of modified derivatives in which, in addition to changes in physicochemical properties, receptor binding is significantly altered, thus a bioactivity different from that of the parent compound predominates. In the frame of this work, 2-arylidene derivatives were first synthesized by regioselective modification of the A-ring of natural sex hormone, 5α-dihydrotestosterone (DHT). After Claisen-Schmidt condensations of DHT with (hetero)aromatic aldehydes in alkaline EtOH, heterocyclizations of the α,β-enones were performed with 3-amino-1,2,4-triazole, 3-aminopyrazole and 3-amino-5-methylpyrazole in the presence of t-BuOK in DMF to afford 7'-epimeric mixtures of A-ring-fused azolo-dihydropyrimidines, respectively.
View Article and Find Full Text PDFDirect N-Selective Alkylation of Hydantoins Using Potassium Bases.
Chem Pharm Bull (Tokyo)
July 2021
Department of Synthetic Organic Chemistry, Graduate School of Biomedical and Health Sciences, Hiroshima University.
Hydantoins, including the antiepileptic drug phenytoin, contain an amide nitrogen and an imide nitrogen, both of which can be alkylated. However, due to the higher acidity of its proton, N can be more easily alkylated than N under basic conditions. In this study, we explored methods for direct N-selective methylation of phenytoin and found that conditions using potassium bases [potassium tert-butoxide (BuOK) and potassium hexamethyldisilazide (KHMDS)] in tetrahydrofuran (THF) gave N-monomethylated phenytoin in good yield.
View Article and Find Full Text PDFWant 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!