The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C-H bond and the formation of a new arene C-N bond. The substitution pattern of the carbazole product can be controlled by the design of the biaryl amide substrate, and the method is compatible with a variety of functional groups. The utility of the new protocol was demonstrated by the concise synthesis of three natural products from commercially available materials.
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http://dx.doi.org/10.1021/jo801273q | DOI Listing |
Molecules
January 2025
Department of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada.
A concise, transition metal-free four-step synthetic pathway has been developed for the synthesis of tetracyclic heterosteroidal compounds, 14-aza-12-oxasteroids, starting from readily available 2-naphthol analogues. After conversion of 2-naphthols to 2-naphthylamines by the Bucherer reaction, subsequent selective C-acetylation was achieved via the Sugasawa reaction and reduction of the acetyl group using borohydride, which resulted into the corresponding amino-alcohols. The naphthalene-based amino-alcohols underwent double dehydrations and double intramolecular cyclization with oxo-acids leading to one-pot formation of a C-N bond, a C-O bond and an amide bond in tandem, to generate two additional rings completing the steroidal framework.
View Article and Find Full Text PDFMolecules
January 2025
School of Environment and Public Health, Xiamen Huaxia University, Xiamen 361024, China.
In this study, we present the HOAc-catalyzed selective cleavage of the C=C double bond of enaminones, enabling the formation of a new C-N bond and a new C=N bond for the one-pot synthesis of 2-substituted 3,4-dihydroquinazolines directly from ynones and 2-(aminomethyl)anilines. This method operates in ethanol under transition-metal-free and oxidant-free conditions, offering a sustainable and efficient approach for the synthesis of 3,4-dihydroquinazolines with broad functional group tolerance.
View Article and Find Full Text PDFChemistry
January 2025
VIT University, Materials Chemistry Division, School of Advanced Sciences, VIT University, 632014, Vellore, INDIA.
Amidines are a vital class of bioactive compounds and often necessitate multiple components for their synthesis. Therefore, exploring efficient and sustainable methodologies for their synthesis is indispensable. Herein, we disclose an alternative and greener method for synthesizing an unexplored new class of amidines through the photochemical synergistic effect of copper/nitroxyl radical catalysis.
View Article and Find Full Text PDFWaste Manag
January 2025
State Key Laboratory of Coal Combustion, School of Energy and Power Engineering, Huazhong University of Science and Technology, Wuhan 430074, China.
Molten salt thermal treatment of solid waste is a promising way for energy recovery and pollutant removal. However, the migration of nitrogen during pyrolysis of waste tires poses a challenge for cleaner production. This study investigated nitrogen conversion pathways during waste tires pyrolysis using a binary NaOH-NaCO salt at 425, 500, and 575 °C.
View Article and Find Full Text PDFJ Agric Food Chem
January 2025
Ankang Research and Development Center for Se-Enriched Products, Ankang 725000, China.
Selenopeptides can be ideal dietary selenium (Se) supplements for humans. Currently, rice is not used much as a source of selenopeptides. Here, we executed the selenopeptidomics analysis of selenium-enriched rice protein hydrolysates using the full MS-dd-MS2 acquisition method and identified selenopeptides, including L{Se-Met}AK and other selenopeptides.
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