A novel and streamlined approach to synthesizing benzotriazepin-1-ones has been developed through a hexafluoroisopropanol-promoted decarboxylative cascade reaction between isatoic anhydrides and hydrazonoyl chloride. The [4 + 3] annulation of hexafluoroisopropyl 2-aminobenzoates with nitrile imines, generated in situ, is a key feature of this innovative reaction. This approach has offered a simple and efficient method for synthesizing a broad range of structurally intricate and highly functional benzotriazepinones.
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http://dx.doi.org/10.1021/acs.joc.3c00524 | DOI Listing |
3 Biotech
January 2025
Peptide and Medicinal Chemistry Research Laboratory, Department of Chemistry, Rani Channamma University, P-B, NH-4, Belagavi, 591 156 India.
Unlabelled: We have developed novel and sustainable homogeneous catalysts employing Glutamic acid (Glu) as a biodegradable and eco-friendly organocatalyst for the synthesis of -(4-oxo-2-phenyl-1,2-dihydroquinazolin-3(4)-yl)isonicotinamide derivatives (-) via multicomponent reactions (MCRs) of isatoic anhydride, isoniazid and heteroaromatic/aromatic aldehyde in ethanol on oil bath stirring at 60 °C. Selected final product homogeneity was examined by various spectroscopic techniques such as C-, H- NMR, FT-IR and LC-MS. For the first time, herein investigated electrochemical behavior of selected derivatives (-) using cyclic voltammetry method.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Sidho-Kanho-Birsha University, Purulia 723104, W.B., India.
Distinctive, green, innovative, and well-organized photoinduced (metal- or photocatalyst-free) regioselective decarbonylative and decarboxylative C-O bond functionalization protocols to access aryl 2-aminobenzoates and 2-substituted benzoxazinone derivatives in excellent yields have been devised. These are achieved through the chemoselective scission of isatoic anhydride with ketones, diaryliodonium triflate, nitroalkene, phthalazinone, and phenol derivatives, which, in turn, served as the representative "electrophilic and nucleophilic" coupling partners. Control experiments and DFT calculations reveal that electrophilic radical-bearing coupling partners specifically follow the decarbonylation pathway, while nucleophilic radical-bearing conjugates facilitate the decarboxylation process.
View Article and Find Full Text PDFRSC Adv
October 2024
Department of Biological Science and Technology, National Yang Ming Chiao Tung University Hsinchu 30010 Taiwan
This report presents the design and synthesis of quinazolinone-based derivatives as promising SARS-CoV-2 3CL protease inhibitors. Two novel series, namely, febrifugine analogues 4a-i and quinazolinone conjugated benzimidazoles 9a-c, were successfully synthesized starting from isatoic anhydride. The synthesized quinazolinone derivatives were evaluated for their cytotoxicity against cancer cell lines and SARS-CoV-2 3CL inhibitory activity.
View Article and Find Full Text PDFHeliyon
October 2024
Department of Chemistry, Payame Noor University, Tehran, Iran.
This research presents a sustainable approach to fabricate iron oxide nanoparticles by employing phytochemicals derived from marine grass extract as both reducing and stabilizing agents. Formation of magnetic nanoparticles (MNPs) initially confirmed by ultraviolet-visible spectroscopy (UV-vis) showing absorption peak at 370 nm. X-ray diffraction (XRD) and transmission electron microscopy (TEM) techniques unveiled magnetic iron oxide NPs with a rod shape, an average size of 21 nm, and an inverse spinel crystal structure.
View Article and Find Full Text PDFChem Commun (Camb)
October 2024
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
Density functional theory calculations uncovered a new mechanism for the rhodium-catalyzed decarbonylative annulation of isatoic anhydride with alkynes, in which the acyloxy group formed from the N-H deprotonation and C-O bond cleavage of isatoic anhydride acts as the directing group to assist the C-H activation. From the generated five-membered rhodacycle intermediate, the final aminoisocoumarin product could be formed by subsequent steps of alkyne insertion, reductive elimination, decarbonylation, and protonation. The isocyanate moiety contained in the annulation intermediate was uncovered as a novel internal oxidant for the reaction, which oxidizes the Rh(I) to Rh(III) by decarbonylation.
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