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A sequential [1 + 2] annulation reaction of indolin-2-imines with α-aryl vinylsulfonium salts has been achieved for the first time, leading to a series of functionalized spiro[cyclopropane-1,3'-indolin]-2'-imines in 51-95% yields with high chemoselectivity and diastereoselectivity. The method is easy to manipulate, operates under mild conditions, and shows wide substrate scope with good functional group tolerance. Moreover, some of the selected spiro-annulated products exhibit promising anticancer activity against the A549 cell line, highlighting their potential for application in drug screening.
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http://dx.doi.org/10.1039/d5ob01012h | DOI Listing |
Org Lett
September 2025
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Wushan Rd-381, Guangzhou 510641, P.R. China.
Herein, we report the first regio- and enantioselective synthesis of tetrahydropyrido[2,3-]pyrazines using a chiral iridacycle catalyst. Pyridyl diamines and diketones undergo sequential annulation and asymmetric transfer hydrogenation of the generated pyrido[2,3-]pyrazine intermediates. This method provides diverse fused N-heterocycles in high yields (up to 95%) and enantioselectivity (98.
View Article and Find Full Text PDFOrg Lett
September 2025
School of Chemistry and Chemical Engineering/Institute of Clean Energy and Materials/Guangzhou Key Laboratory for Clean Energy and Materials, Guangzhou University, Guangzhou 510006, P. R. China.
The facile synthesis of indole-fused diazepinones via Rh(III)-catalyzed [4 + 3] annulation of indole derivatives with cyclopropyl alcohol by merging sequential C-H and C-C bond cleavage has been realized. Notably, the eight-membered diazocino[7,8,1-]indol-5-ones and seven-membered azepino[3,4-]indol-1(2)-ones could also be obtained via this tandem reaction strategy. This catalytic approach features mild reaction conditions, readily accessible starting materials, valuable products, and excellent atom-economy.
View Article and Find Full Text PDFOrg Lett
August 2025
Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, College of Chemistry & Chemical Engineering, Anhui University, Hefei, Anhui 230601, China.
α-Diazo sulfonium salts constitute a unique subclass of diazo reagents that integrate diazo and sulfonium functionalities within a single molecular scaffold. While their reactivity via carbene, radical, or carbyne intermediates has been extensively investigated, the synthetic utility of their proton-activated dicationic species remains largely unexplored. Herein, we report a Brønsted acid-promoted, metal-free annulation of α-diazo sulfonium salts with binucleophilic α-vinylanilines.
View Article and Find Full Text PDFChem Commun (Camb)
August 2025
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, India.
Rh-catalyzed C-H functionalization/annulation of arylamides with maleimides has been accomplished to furnish succinimide-tethered isoquinoline-1,3-diones. The sequential C-C/C-N bond formation, substrate scope, access to quaternary carbon and functional group tolerance are the salient features.
View Article and Find Full Text PDFJ Am Chem Soc
August 2025
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, People's Republic of China.
The development of organic light-emitting diode (OLED) materials requires precisely engineered molecular architectures with tailored optoelectronic properties. Here, we present a strategy that synergistically integrates diversity-oriented synthesis (DOS) with virtual screening to systematically explore the chemical space of diaza-polycyclic aromatic hydrocarbons (diaza-PAHs) for OLED applications. DOS, originally developed for drug discovery, serves as a powerful tool to generate structurally diverse molecular libraries, granting access to previously unexplored diaza-PAHs with potential OLED functionality.
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