In this work an efficient one-pot synthesis of substituted pyrroles 7a-n is described, which involves the in situ formation of dihydrofurans ethyl 5-butoxy-2-methyl-4,5-dihydrofuran-3-carboxylate (4), 1-(5-butoxy-2-methyl-4,5-dihydrofuran-3-yl)ethanone (5) and 5-butoxy-4,5-dihydrofuran-3-carbaldehyde (6) followed by reaction with primary amines.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2605617 | PMC |
http://dx.doi.org/10.3762/bjoc.4.45 | DOI Listing |
Org Lett
January 2025
China Guangxi Key Laboratory of Pharmaceutical Precision Detection and Screening, Guangxi Key Laboratory of Bioactive Molecules Research and Evaluation, and Key Laboratory of Micro-Nanoscale Bioanalysis and Drug Screening of Guangxi Education Department, Pharmaceutical College, Guangxi Medical University, Nanning 530021, China.
Herein, a one-pot domino catalyzed three-component process is described, which is initiated by a palladium/zinc cooperatively catalyzed cycloaddition between trimethylenemethane (TMM) and unactivated alkyl/aryl imines, followed by one-pot isomerization and Zn(OTf)-catalyzed DDQ oxidation, furnishing valuable substituted pyrroles. We disclose that the palladium/zinc cooperative catalysis affords a dual-Zn(OTf)-stabilized azapalladacycle, wherein the Pd-N bond is polarized by Zn(OTf), facilitating a unique outer-sphere allylic amination. Moreover, subsequent DDQ dehydrogenation can be feasibly promoted by zinc catalysis.
View Article and Find Full Text PDFEur J Med Chem
December 2024
School of Pharmaceutical Sciences, Lovely Professional University, Phagwara, 144411, India. Electronic address:
This study presents a comprehensive exploration of the synthesis of novel compounds targeting Chagas Disease (CD) caused by Trypanosoma cruzi. It is a global health threat with over 6-7 million infections worldwide. Addressing challenges in current treatments, the investigation explores diverse compound classes, including thiazoles, thiazolidinone, imidazole, pyrazole, 1,6-diphenyl-1H-pyrazolo[3,4-b] pyridine, pyrrole, naphthoquinone, neolignan, benzeneacyl hydrazones, and chalcones-based compounds.
View Article and Find Full Text PDFNat Commun
December 2024
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China.
The functionalized polycycle with densely contiguous tertiary stereocenters is a formidable challenge in synthesizing the parvistemoline family of Stemona alkaloids. We herein report their catalytic, asymmetric total syntheses in 13-14 steps from commercially available 2-(methoxycarbonyl)-pyrrole, featuring the development and deployment of an Ir/Pd-synergistically-catalyzed allylation of α-non-substituted keto esters with secondary aryl-substituted alcohols, stereodivergently accessible to four stereoisomers. Using chiral Pd-enolate and Ir π-allyl complex under neutral conditions, no epimerization occurs.
View Article and Find Full Text PDFChemistry
December 2024
Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 53210, Czech Republic.
Differently substituted pyrrole-azo-benzene molecular photoswitches were prepared in a straightforward synthetic way. Their fundamental properties were investigated by XRD analysis, differential scanning calorimetry, thermogravimetric analysis, cyclic voltammetry, UV-Vis absorption spectroscopy, Hyper-Rayleigh Scattering, and NMR spectroscopy; the experimental results were further corroborated by DFT calculations. Thermal robustness, the HOMO/LUMO levels, and the absorption properties were altered mostly by substituting the N-methylpyrrole moiety and further fine-tuned by modifying the benzene substituents.
View Article and Find Full Text PDFChem Asian J
December 2024
Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur Botanic Garden, Howrah, 711103, India.
Herein, we describe a sustainable Co(II)-catalyzed synthesis of pyrroles and pyridines. Using a Co(II)-catalyst [Co (L)Cl] (1 a) bearing redox-active 2-(phenyldiazenyl)-1,10-phenanthroline) (L) scaffold, various substituted pyrroles and pyridines were synthesized in good yields, taking alcohol as one of the primary feedstock. Pyrroles were synthesized by the equimolar reaction of 2-amino and secondary alcohols.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!