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In this work, we demonstrate the synthesis of a variety of 2,5-disubstituted 1,3,4-thiadiazoles in 28-85% yields three-component cyclization of 2-methylquinolines, arylhydrazides, and S powder under metal-free conditions. This approach stands out due to its broad substrate scope, excellent functional group tolerance, additive-free nature, base-free nature, easy operation, and simple reaction system. This work offers a simple, concise, and convenient pathway for the assembly of a variety of 1,3,4-thiadiazoles, which is complementary to previous methods.
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http://dx.doi.org/10.1039/d5ob00554j | DOI Listing |
J Org Chem
September 2025
National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650500, P. R. China.
We herein describe a novel decarboxylation/cyclization sequence involving a three-component reaction of dialkyl 2-(alkoxymethylene)malonate, amines, and terminal alkyne ester or internal alkyne ester catalyzed by CsCO under microwave conditions. These two types of highly chemo- and regioselective transformations were accomplished by different reaction channels to furnish a wide range of functionalized 8-hydroxyisoquinoline-1(2)-ones (21 examples) and 2-pyridones (18 examples) in good to excellent yields and might provide new opportunities for the discovery of N-heterocyclic drugs and other functional molecules.
View Article and Find Full Text PDFJ Org Chem
September 2025
School of Chemistry and Chemical Engineering, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China.
Radical cascade cyclization of alkenes involving the insertion of sulfur dioxide has proven to be a promising tool to access sulfonylnated heterocycle compounds, whereas cyclization of unactivated alkenes has been much less explored. Here, we developed a three-component cascade of unactive alkenes with sulfur dioxide and aryldiazonium tetrafluoroborates to generate sulfonylated tetrahydropyridines and azepines via the cleavage of alkenyl C-H bonds. Moreover, this protocol exhibited excellent chemical and regioselectivity and compatibility with broad functional groups.
View Article and Find Full Text PDFChem Commun (Camb)
September 2025
College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. China.
A palladium-catalyzed divergent three-component reaction employing norbornene derivatives as controlled switches toward phosphonate-containing indenes and indanes was established. When using norbornadiene, norbornene or 7-oxabenzonorbornadiene as a substrate, alkylphosphonate-containing indanes were synthesized through a cascade [3+2] cyclization and alkylation of P(O)H process. Alternatively, oxanorbornadiene enabled the assembly of phosphonate-containing indenes a subsequent retro-Diels-Alder reaction.
View Article and Find Full Text PDFJ Org Chem
August 2025
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China.
This study presents a Rh(III)-catalyzed C-H activation/[5 + 2] cyclization strategy for the efficient synthesis of benzo[]pyrazolo[1,5-][1,3]diazepines (BPDs) . The [Cp*RhCl]/AgTFA catalytic system enables the one-step construction of azepane-fused polycycles from 5-amino-1-arylpyrazole and iodonium ylides. Expansion to a three-component reaction was achieved by adjusting the catalyst/additive ratio and incorporating alcohol substrates, enabling the synthesis of BPDs .
View Article and Find Full Text PDFChem Commun (Camb)
August 2025
School of Environmental and Chemical Engineering, Wuyi University, Jiangmen 529020, China.
This article presents a metal-free catalytic system for the [4+2] cycloaddition of isoquinoline and maleimide derivatives, enabling the one-step construction of structurally complex bridged polycyclic lactams. This three-component tandem cyclization reaction generates C-N, CO, and C-C bonds, achieving functionalization at the C1, N2, C3, and C4 positions of 3-halogenated isoquinolines. This dearomatization strategy exhibits exceptional chemoselectivity and regioselectivity, operates without transition metals, and offers a high atom and step economy.
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