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The annulation reaction of β-methyl enaminones with alkynones leading to the synthesis of methylene-functionalized 1,2-dihydropyridines (1,2-DHPs) has been realized. In the presence of only CsCO, 1,2-DHPs have been synthesized with a broad scope and generally high efficiency via the novel transformation of the γ-C(sp)-H bond in enaminones. In addition, the application of the method has been demonstrated by the one-step transformation of the 1,2-DHP products into fused tricyclic scaffolds featuring an indole-pyridine hybrid via dual C-H activation.
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http://dx.doi.org/10.1021/acs.orglett.5c03269 | DOI Listing |
Org Lett
September 2025
Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, United States.
Herein, we report the first asymmetric synthesis of cycloartobiloxanthone, a polycyclic dihydroxanthone natural product. Our convergent synthesis employs a rhodium-catalyzed C-H insertion reaction to construct the key fused tricyclic core with high enantioselectivity. Two fragments were joined together by a displacement reaction and a Friedel-Crafts acylation to generate the dihydroxanthone core.
View Article and Find Full Text PDFOrg Lett
September 2025
Jiangxi Province Key Laboratory of Natural and Biomimetic Drugs Research, College of Chemistry and Materials, Jiangxi Normal University, Nanchang 330022, China.
The annulation reaction of β-methyl enaminones with alkynones leading to the synthesis of methylene-functionalized 1,2-dihydropyridines (1,2-DHPs) has been realized. In the presence of only CsCO, 1,2-DHPs have been synthesized with a broad scope and generally high efficiency via the novel transformation of the γ-C(sp)-H bond in enaminones. In addition, the application of the method has been demonstrated by the one-step transformation of the 1,2-DHP products into fused tricyclic scaffolds featuring an indole-pyridine hybrid via dual C-H activation.
View Article and Find Full Text PDFJACS Au
August 2025
College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
The generation of metal carbenes from readily available allenes represents a remarkable advance in metal carbene chemistry. However, most of these transformations are mainly restricted to the noble-metal catalysts (Au and Pt). Here, a copper-catalyzed desymmetric cyclization reaction of divinylallenes is described, enabling the practical and atom-economical synthesis of a diverse array of valuable triazolo-fused pyridazines and tetracyclic N-heterocycles by a presumable copper carbene intermediate and a highly selective 1,2-N shift process.
View Article and Find Full Text PDFChemistry
August 2025
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, Assam, 781039, India.
A Brønsted acidic ionic liquid (BAIL)-catalyzed one-pot tandem reduction of quinoline to tetrahydroquinoline (THQ) followed by reductive alkylation by the aldehyde has been demonstrated under mild reaction conditions with a shorter reaction time. This step-economical synthetic approach is suitable for late-stage functionalization of complex bioactive molecules. The reaction is highly chemoselective and tolerates a wide range of reducible-sensitive functional groups.
View Article and Find Full Text PDFOrg Lett
August 2025
Jiangxi Provincial Key Laboratory of Synthetic Pharmaceutical Chemistry, Gannan Normal University, Ganzhou 341000, China.
A novel palladium-catalyzed dearomative cyclization of naphthalenes and benzenes has been accomplished for the expedient construction of fused polycyclic skeletons bearing an all-carbon quaternary center. Excellent functional group tolerance was demonstrated in the reaction of 2,2-phenylnaphthyl acetonitriles, in which the cyano group can serve as a linkage for potential applications. In addition, the challenging dearomatization of benzenes was developed, offering [6,5,6]-carbotricyclic scaffolds that may play a role as an intermediate for the synthesis of fused tricyclic natural products and analogues.
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