The active six-membered cyclo-FLP 6 undergoes a rapid P/B addition reaction to carbon dioxide. At elevated temperature, the resulting heterobicyclo[2.2.2]octane derived product 7 undergoes ring opening and equilibrates with the cyclotetramer (7) . In the large macrocyclic structure, four monomeric six-membered cyclo-FLP units are connected by four CO molecules to form the supramolecular ring system. The P/B cyclo-FLP 6 undergoes a variety of additional cycloaddition reactions.
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http://dx.doi.org/10.1002/chem.201905171 | DOI Listing |
J Mol Model
January 2025
Departamento de Investigación y Desarrollo, ConsultoresAcademicos SpA, Moneda 1137, 8340457, Santiago, Chile.
Context: This study meticulously examines the criteria for assigning electron rearrangements along the intrinsic reaction coordinate (IRC) leading to bond formation and breaking processes during the pyrolytic isomerization of cubane (CUB) to 1,3,5,7-cyclooctatetraene (COT) from both thermochemical and bonding perspectives. Notably, no cusp-type function was detected in the initial thermal conversion step of CUB to bicyclo[4.2.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Key Laboratory of Evolution & Marine Biodiversity (Ministry of Education) and Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, China.
Dihydronaphthalenes play a crucial role in bioactive natural products and new drug discovery, and efficient and economic strategies to build them are needed. Herein, we disclose a highly efficient method to prepare dihydronaphthalenes a cerium-catalyzed cycloaddition of 1-isochromenes with cinnamic acids. This newly developed method not only features a broad and low-cost substrate scope and mild conditions but also exhibits very high functional group tolerance, including hydroxyl, borate ester and ester group substituents.
View Article and Find Full Text PDFChem Sci
December 2024
Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong Pokfulam Road Hong Kong P. R. China
Phosphorescent gold(iii) complexes possess long-lived emissive excited states, making them ideal for use as molecular sensors and photosensitizers for organic transformations. Literature reports indicate that gold(iii) emitters exhibit good catalytic activity in homogeneous photochemical reactions. Heterogeneous metal-organic framework (MOF)-supported gold(iii) photocatalysts are considered to show high recyclability in photochemical reactions and potentially provide new selectivities.
View Article and Find Full Text PDFBioorg Chem
January 2025
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentyev Avenue 9, Novosibirsk 630090, Russia. Electronic address:
Eudesmane-type sesquiterpene lactone isoalantolactone 1 is of great interest due to its availability, biological activity and synthetic application. Respective series of original spirocyclic (11S,5') (1,2,3-triazoline-eudesma-4,15-enolides) and (11S)-aziridine-eudesma-4,15-enolides were efficiently synthesized via a chemoselective 1,3-dipolar cycloaddition reaction of organic azides to the exocyclic double bond of the lactone ring of isoalantolactone or 13E-(aryl)isoalantolactones by heating in DMF or toluene. The thermal reactions of isoalantolactone with benzyl azide, 2-azidoethanol, or n-butyl azide in 2-methoxyethanol afforded 13-(alkyamino)isoalantolactones formed as a mixture of (Z) and (E)-isomers.
View Article and Find Full Text PDFBioorg Chem
January 2025
Department of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002 Saudi Arabia. Electronic address:
The discovery of novel anti-cancer drugs motivated us to synthesize a new series of triple 1,2,3-triazole-based arm scaffolds featuring distinct un functionalized alkyl and/or aryl side chains with possible anti-cancer action using the click chemistry approach under both conventional and green microwave irradiation (MWI) methods. The Cu(I) catalyzed cycloaddition reaction of targeted tris-alkyne with un functionalized aliphatic and aromatic azides has been adopted as an efficient approach for synthesizing the desired click adducts. Microwave irradiation improved the synthetic processes, resulting in higher yields and faster reaction times.
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