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One-step DMAP-catalyzed [3 + 2] and [4 + 2] cycloaddition reactions between C(60) and unmodified Morita-Baylis-Hillman adducts in the presence of Ac(2)O have been developed for the easy preparation of cyclopentene- and cyclohexene-fused [60]fullerene derivatives. When the MBH adducts bear an alkyl group, two different reaction pathways could be controlled selectively depending on the conditions.
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http://dx.doi.org/10.1021/jo3025797 | DOI Listing |
Org Lett
November 2024
School of Pharmaceutical Sciences & Institute of Materia Medica, Medical Science and Technology Innovation Center, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan, Shandong 250117, P. R. China.
The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives with moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction of vinyl epoxides, simultaneously providing a rare oxygen-containing active intermediate in this field. The gram-scale preparation and facile derivatization of the cycloadduct highlight the significant synthetic potential of this strategy.
View Article and Find Full Text PDFChem Asian J
March 2024
Department of Chemistry and Chemical Biology, Indian Institution of Technology (Indian School of Mines), Dhanbad, 826004, Dhanbad (Jharkhand), India.
An efficient and practical method for the N-alkynylation of 7-azaindoles has been established by using CuI/DMAP catalytic system at room temperature and in open air. This simple protocol has been successfully employed in the synthesis of a wide range of N-alkynylated 7-azaindoles with good yields. Also, this approach is well-suited for large-scale N-alkynylation reactions.
View Article and Find Full Text PDFMolecules
April 2023
Department of Chemistry and Research Institute of Basic Sciences, Incheon National University, Incheon 22012, Republic of Korea.
The framework of 1,3,4-oxadiazine is crucial for numerous bioactive molecules, but only a limited number of synthetic methods have been reported for its production. In 2015, Wang's group developed a 4-(dimethylamino)pyridine (DMAP)-catalyzed [2 + 4] cycloaddition of allenoates with -acyldiazenes, which provided an atom-efficient route for 1,3,4-oxadiazines. However, the practicality of this method was limited by the instability of -acyldiazenes as starting materials.
View Article and Find Full Text PDFOrg Lett
July 2015
†Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P.R. China.
An efficient DMAP-catalyzed [2 + 4] cycloaddition of allenoates and N-acyldiazenes is reported. The reaction involved embedding three heteroatoms into a six-membered ring and generated 1,3,4-oxadiazine derivatives in moderate to good yields.
View Article and Find Full Text PDFJ Org Chem
February 2013
School of Petrochemical Engineering, Changzhou University, Changzhou 213164, People's Republic of China.
One-step DMAP-catalyzed [3 + 2] and [4 + 2] cycloaddition reactions between C(60) and unmodified Morita-Baylis-Hillman adducts in the presence of Ac(2)O have been developed for the easy preparation of cyclopentene- and cyclohexene-fused [60]fullerene derivatives. When the MBH adducts bear an alkyl group, two different reaction pathways could be controlled selectively depending on the conditions.
View Article and Find Full Text PDF