A rhodium-catalyzed annulation of 2-azirines with enaminones is presented. This protocol affords a convenient approach to the diversity-oriented synthesis of 4-acyl- and 4-formyl pyrroles with good functional group tolerance. The utility of this reaction has been demonstrated by scale-up preparation, late-stage modification of natural molecules, and synthesis of diverse derivatives.
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http://dx.doi.org/10.1021/acs.orglett.5c00230 | DOI Listing |
Org Biomol Chem
February 2025
Glycochemistry Laboratory, School of Physical Sciences, Jawaharlal Nehru University, New Delhi-110067, India.
Herein, we report a highly efficient organobase-catalyzed method for the synthesis of fully decorated chiral 4-acyl-5-aryl-trisubstituted-1,2,3-triazole-linked -glycosidic molecular scaffolds as glycohybrids. This process involves a base-catalyzed 1,3 dipolar cycloaddition reaction, where β-ketoesters react with various glycosyl azides in dimethyl sulfoxide at room temperature, furnishing new glycohybrids in good to excellent yields. This intermolecular reaction is metal-free, exceptionally efficient, versatile, and high-yielding, with a broad substrate scope and remarkable regioselectivity.
View Article and Find Full Text PDFOrg Lett
February 2025
National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Province Key Laboratory of Natural and Biomimetic Drugs Research, College of Chemistry and Materials, Jiangxi Normal University, Nanchang, Jiangxi 330022, China.
A rhodium-catalyzed annulation of 2-azirines with enaminones is presented. This protocol affords a convenient approach to the diversity-oriented synthesis of 4-acyl- and 4-formyl pyrroles with good functional group tolerance. The utility of this reaction has been demonstrated by scale-up preparation, late-stage modification of natural molecules, and synthesis of diverse derivatives.
View Article and Find Full Text PDFJ Tradit Chin Med
December 2024
State Key Laboratory for Quality Ensurance and Sustainable Use of Dao-di Herbs, Artemisinin Research Center, and Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China.
Objective: To investigate the efficacy and potential mechanism of Bailing capsule (, BL) anti-autoimmune thyroiditis (AIT).
Methods: Based on the AIT rat model, the effect of BL in alleviating AIT was evaluated by detecting serum thyroid index free triiodothyronine (FT3), free thyroxine (FT4), thyroid-stimulating hormone (TSH), thyroglobulin antibody (TGAb), thyroid peroxidase antibody (TPOAb), and inflammatory factors Interferon-gamma (IFN-γ), Interleukin-4, -10, and -12 (IL-4, IL-10, and IL-12) as well as thyroid tissue Hematoxylin-eosin (HE) staining and ultrastructure observation. The mechanism of BL was explored by combining transcriptome and proteome analysis, and further verified by Western blot (WB).
Chemistry
December 2024
Synthetic Organic Chemistry, Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ, Nijmegen, the, Netherlands.
A key challenge in oligosaccharide synthesis is the stereoselective installation of glycosidic bonds. Each glycosidic linkage has one of two possible stereo-chemical geometries, α/β or 1,2-cis/trans. An established approach to install 1,2-trans glycosidic bonds is neighboring group participation (NGP), mediated by a 2-O-acyl group.
View Article and Find Full Text PDFJ Org Chem
September 2024
Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan.
,-Dimethylformamide was reacted with hexamethyldisilazane to generate an ,-dimethylformimidamide intermediate; thereafter, a reaction with acetophenones/β-diketones was induced to form enaminones. The one-pot synthetic protocol described in this paper can be applied to synthesize 1,4-disubstituted 1,2,3-triazoles and 1,4,5-trisubstituted 1,2,3-triazoles, in which organic azides are used as substrates under optimized conditions. Furthermore, this protocol uses readily available materials, is nearly free of solvent, can be applied to gram-scale operations, and leads to the formation of structurally diverse products with favorable yields.
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