The reaction of 5-substituted 2-nitrosophenols with bromomethyl aryl ketones and related compounds employing K2CO3 as a base in refluxing THF and DMF at 80 °C, respectively, delivers 2-aroylbenzoxazoles in a single step with yields up to 85%. The new method involves an intermolecular nucleophilic substitution followed by intramolecular 1,2-addition and elimination. It allows an efficient and practical access to 2-aroylbenzoxazoles under transition-metal-free conditions.
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http://dx.doi.org/10.1021/acs.joc.5b02000 | DOI Listing |
Int J Mol Sci
November 2024
Department of Bioorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland.
We have previously shown that 2-thiouridine (S2U), either as a single nucleoside or as an element of RNA chain, is effectively desulfurized under applied in vitro oxidative conditions. The chemically induced desulfuration of S2U resulted in two products: 4-pyrimidinone nucleoside (H2U) and uridine (U). Recently, we investigated whether the desulfuration of S2U is a natural process that also occurs in the cells exposed to oxidative stress or whether it only occurs in the test tube during chemical reactions with oxidants at high concentrations.
View Article and Find Full Text PDFNanoscale Adv
October 2024
Department of Medical Engineering, Al-Nisour University College Baghdad Iraq.
In this study, we have prepared a novel bis-Schiff-base copper(ii) complex by modifying FeO with acetylacetone functionalities and subsequently forming a Schiff base with 2-picolylamine and CuCl through a template method. Immobilization of 2,4-pentanedione and its reaction with 2-picolylamine enabled the synthesis of 1,3-diketimines (HNacNac) as an anionic ligand. This unique design resulted in a tetradentate N coordination sphere for copper(ii) ion complexation.
View Article and Find Full Text PDFPhys Chem Chem Phys
November 2024
Department of Nanoscience, Joint School of Nanoscience and Nanoengineering University of North Carolina at Greensboro, Greensboro, NC 27401, USA.
An aromatic boron-containing organic compound, CBH, with an unusual CC bond was experimentally synthesized in 2017. Here we investigate the structure and bonding nature of CBH and its derivatives CBR using DFT and VB theory. Although the CC bond in CBR consists of a π bond and a charge-shift (CS) bond, CBF has the lowest LUMO energy and its LUMO is similar to that of ethylene, suggesting that CBF can be an ideal dienophile for the Diels-Alder reaction.
View Article and Find Full Text PDFPrecis Chem
March 2024
Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan.
γ-Butyrolactone structures are commonly found in various natural products and serve as crucial building blocks in organic synthesis. Consequently, the development of methods for synthesizing γ-butyrolactones has garnered significant interest within the organic synthesis community. In this study, we present a direct and highly efficient approach for the synthesis of γ-butyrolactones from allylic alcohols.
View Article and Find Full Text PDFJ Org Chem
October 2024
Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.
An approach to a new type of diazo reagents─diazo dihydrouracils─has been developed, and various transformations of the obtained diazo heterocycles have been studied, demonstrating their high synthetic potential for obtaining structurally diverse derivatives based on the privileged dihydrouracil scaffold. The X-H insertion reactions provide high yields of a variety of 5-substituted dihydrouracils. Cyclopropanation and 1,3-dipolar cycloaddition reactions involving a carbonyl ylide intermediate have been carried out to give spiro-annulated derivatives.
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