98%
921
2 minutes
20
Racemic 2-(2,4-dinitrophenyl)hydrazono)-5,6-diphenyl-1,3-thiazinan-4-ones and (Z)-N'-(2,4-dinitrophenyl)-2,3-diphenylacrylohydrazide were formed during the diastereoselective reaction between 4-substituted 1-(2,4-dinitrophenyl)thiosemicarbazides and 2,3-diphenylcycloprop-2-enone under refluxing ethanol. The structures of the synthesized compounds were confirmed by single-crystal X-ray analyses.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1007/s11030-018-09912-5 | DOI Listing |
J Org Chem
September 2025
Department of Chemistry, China Agricultural University, Beijing 100193, P. R. China.
This study presents a phosphine-catalyzed [3 + 2] annulation of sulfamidate imine-derived 1-azadienes with Morita-Baylis-Hillman (MBH) carbonates or allenoates, affording densely functionalized spiro[oxathiazole-cyclopentene] architectures under mild reaction conditions in generally high yields and excellent diastereoselectivities. Through a reductive ring contraction sequence of the spirocyclic thiosulfamide, valuable spirocyclic aziridine derivatives were accessed conveniently via both two-step and one-pot protocols.
View Article and Find Full Text PDFEur J Med Chem
November 2025
Department of Infectious Diseases, Kumamoto University School of Medicine, Kumamoto, 860-8556, Japan; Center for Clinical Sciences, National Center for Global Health and Medicine, Tokyo, 162-8655, Japan; Experimental Retrovirology Section, HIV and AIDS Malignancy Branch, National Cancer Institute, N
We report here the design, synthesis and evaluation of a series of HIV-1 protease inhibitors that incorporate substituted oxaspirocyclic carbamate derivatives to serve as the P2 ligands. Various substituted ligand derivatives were synthesized in a racemic manner, using a tandem Prins/pinacol reaction as the key reaction. This reaction sets the relative stereochemistry of the oxaspirocyclic template in a highly diastereoselective manner.
View Article and Find Full Text PDFChem Sci
August 2025
Fakultät Chemie und Biochemie, Organische Chemie I, Ruhr-Universität Bochum Universitätsstr. 150 44801 Bochum Germany
The palladium-catalyzed diastereoselective arylation of Schöllkopf bis-lactim ethers has recently emerged as a convenient entry to enantioenriched arylglycine derivatives. Key limitations of the prototypical protocol have now been overcome by the use of the customized, diadamantyl-substituted -coordinating ylide-functionalized phosphine ligand adYPhos. Catalyst generated from 1-methylnaphthyl palladium bromide dimer and adYPhos effectively promote the coupling of aryl chlorides with a commercially available, valine-based Schöllkopf-reagent in 97% yield and a diastereoselectivity of 98 : 2.
View Article and Find Full Text PDFJ Org Chem
June 2025
Department of Chemistry, Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, United States.
We report highly diastereoselective TiCl-mediated tandem reactions that provide functionalized tricyclic benzocycloheptafurans in an efficient manner. The reaction of a range of substituted α-keto esters with dihydrofuran or phenyl dihydrofuran in CHCl set up a tandem reaction sequence, providing fused ring heterocycles. The precursor-substituted keto esters were synthesized efficiently by using a two-step sequence.
View Article and Find Full Text PDFOrg Biomol Chem
June 2025
Centre for Glycoscience and School of Chemical and Physical Sciences, Keele University, Keele, Staffordshire, ST5 5BG, UK.
An -glycosylation method for accessing coumarin glycosides is presented. We report the reaction of 6,8-difluoro-7-hydroxy-4-methylcoumarin and 4-methylumbelliferone with a variety of glycosyl imidate donors using BF·EtO as activator to access a series of coumarin glycosides in 64%-76% isolated yields. Several reaction parameters are evaluated including promotors, temperature and reagent equivalents.
View Article and Find Full Text PDF