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An effective and straightforward Ag(I)-mediated annulation of 2-(2-enynyl)quinolines and -(2-alkynylbenzylidene)hydrazides was developed, forging various synthetically challenging 17-isoquinolino[2'',1'':1',6']pyridazino[4',5':3,4]pyrrolo[1,2-]quinolines, including different nitrogen-containing fused rings, in moderate to excellent yields. This one-pot cycloaddition strategy features exclusive regioselectivity, high atom economy, and broad substrate scope under mild conditions. The practicality and reliability of this cycloaddition reaction was demonstrated by a successful scale-up synthesis.
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http://dx.doi.org/10.1021/acs.joc.4c01264 | DOI Listing |
Org Lett
August 2025
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, University Engineering Research Center for Chemistry of Characteristic Medicinal Resources (Guangxi),
A variety of indole-fused bicyclo[3.1.1]heptanes were prepared in good yields with high regioselectivity through organocatalyzed umpolung (3+3) cycloaddition of 2-indolylmethanols and bicyclo[1.
View Article and Find Full Text PDFOrg Lett
August 2025
Key Laboratory of Organic Catalysis for Pharmaceutical Intermediates in the Petroleum and Chemical Industry, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
A ring expansion strategy for the synthesis of diverse homopiperazin-5-ones and 1,4-diazocine-5-ones is described. Imidazolidines undergo Zn(OTf)-catalyzed ring expansion with cyclobutenones to produce homopiperazin-5-one derivatives. Alternatively, Cu(MeCN)BF-catalyzed (5 + 3) cycloaddition between imidazolidines and diarylcyclopropenones provides access to eight-membered 1,4-diazocine-5-ones under mild conditions.
View Article and Find Full Text PDFJ Org Chem
August 2025
School of Chemistry and Environmental Engineering, Yancheng Teachers University, Yancheng 224007, People's Republic of China.
This paper presents a novel, environmentally friendly, and efficient method for the construction of new thiazole disulfide skeletons via a domino formal (2 + 3) cycloaddition/self-oxidation reaction. Compared to previously reported methods, this approach offers several advantages, including eco-friendly solvents, mild reaction conditions, and a wide range of applicable substrates. We successfully synthesized a variety of thiazole disulfides with promising potential applications including their use in the late-stage functionalization of pharmaceuticals and natural products.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2025
Department of Chemistry, and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P.R. China.
We present an asymmetric formal total synthesis of pseudolaric acid B (PAB), based on the intramolecular (4+3) cycloaddition of a new class of epoxy enolsilane substrates. This substrate type has the epoxide geminally-substituted on the tether to the furan, which reacts to yield the trans-fused perhydroazulene core of PAB containing the quaternary stereocenter. The reaction is highly diastereoselective, as opposed to cycloadditions of previous substrate types that generate the perhydroazulene framework.
View Article and Find Full Text PDFRSC Med Chem
July 2025
Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science & Technology (KIOST) Busan 49111 Republic of Korea
We report the design and synthesis of thieno[3,2-]pyridin-5(4)-one derivatives exhibiting site-dependent modulation of both antitumor activity and fluorescence, enabled by a regioselective BOP-promoted aza-[3 + 3] cycloaddition. The reaction proceeds between thiophen-3-amines and α,β-unsaturated carboxylic acids, followed by base-induced dehydrogenation. Mechanistic studies reveal that the head-to-tail aza-[3 + 3] annulation involves a -1,4 conjugate addition, leading to an intramolecular amide coupling.
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