Vindoline and its analogues are important constituents of the Madagascan periwinkle Catharanthus roseus, and some of them are valuable chemotherapy drugs used in treatment for some types of cancer, including leukaemia, lymphoma, breast and lung cancer. The search for semi-synthetic congeners of natural substances is still an important task for organic chemistry. In this communication we report the synthesis of five new vindoline derivatives, 15-(2-methoxyphenyl)vindoline 11, 15-(3-methoxyphenyl)vindoline 12, 15-(2-nitrophenyl)vindoline 13, 15-(3-cyanophenyl)vindoline 15, and 15-(4-cyanophenyl)vindoline 16 using the Suzuki-Miyaura reaction as the key step. X-Ray analysis of compound 16 is also reported.
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Molecules
December 2024
Laboratoire de Chimie de Coordination, CNRS, Toulouse-INP, Université de Toulouse, 31000 Toulouse, France.
In recent years, there has been growing interest in the development of greener alternatives to traditional reagents used in carbon-carbon coupling reactions, particularly in response to environmental concerns. The commonly used aryl halides, despite being highly reactive in the Suzuki-Miyaura coupling (SMC), pose significant environmental risks. As a result, research has shifted towards exploring the use of phenols, which are widely accessible and environmentally benign.
View Article and Find Full Text PDFChem Asian J
January 2025
Huazhong University of Science and Technology, School of Chemisry & Chemical Engineering, 1037 Luoyu Road, 430074, Wuhan, CHINA.
Using a direct knitting strategy, we successfully prepared a novel heterogeneous catalyst consisting of pyridine-bridged bis(imidazolium-2-ylidene) palladium complexes (CNC-Pd) embedded in a knitted network polymer. The resulting catalysts (HCP-CNC-Pd-d) exhibited high specific surface areas of 982 m2 g-1 with microporous and mesoporous structures. The large surface area enhances contact between the substrate and the catalytic center, while the strong chelation between CNC and the metal ion ensures the catalyst's durability.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Chemistry, CMS College Kottayam (Autonomous), Kottayam, Kerala, 686001, India.
The Suzuki-Miyaura Coupling (SMC) reaction is a powerful method for forming carbon-carbon bonds in organic synthesis. Recent advancements in SMC reactions have introduced first-row transition metal catalysts, with zinc garnering significant interest due to its cost-effective and eco-friendly nature. Despite progress in experimental protocols, the mechanistic details of zinc-catalyzed SMC reactions are limited.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Osaka University: Osaka Daigaku, Department of Applied Chemistry, JAPAN.
Although numerous transition-metal catalyzed cross-coupling reactions of alkenyl electrophiles with a sulfur(VI) leaving group, mainly alkenyl sulfones, have been developed, most rely heavily on highly nucleophilic Grignard reagents, and the use of organoboron reagents remains challenging. We report herein facile preparation and the following Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of alkenyl sulfoximine, a monoaza analog of sulfone. The condensation of alkyl sulfoximine with aldehydes, developed in this study, makes alkenyl sulfoximines more readily available.
View Article and Find Full Text PDFJ Org Chem
January 2025
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149 Münster, Germany.
Xanthine nucleosides play a significant role in the expansion of the four-letter genetic code. Herein, 7-functionalized 8-aza-7-deazaxanthine ribo- and 2'-deoxyribonucleosides are described. 2-Amino-6-alkoxy nucleosides were converted to halogenated 8-aza-7-deazaxanthine nucleosides by deamination followed by hydroxy/alkoxy substitution.
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