With the aid of acetic acid, a 1,10-conjugate addition-mediated formal [3 + 3] cyclization of alkynyl indole imine methides formed from α-(6-indolyl) propargylic alcohols with 1,3-dicarbonyl compounds such as 4-hydroxycoumarins and cyclohexane-1,3-diones was developed, which provided robust access to a wide range of pyranocoumarin and pyran derivatives containing an indole skeleton with high efficiency under mild conditions.
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http://dx.doi.org/10.1039/d2ob01206e | DOI Listing |
Chemistry
January 2025
Zhengzhou University, School of Pharmaceutical Sciences, 100 Science Avenue, 450001, Zhengzhou, CHINA.
An unprecedented formal [1+5] cyclization of indoline-derived azadienes with 1,3,5-triazinanes has been realized, providing a facile access to biologically important indoline-spiro-hexahydropyrimidines with good to excellent yields (up to 99% yield). Different from previous reports, this is the first study that indoline-derived azadienes could participate in cyclizations as one-atom synthons. This methodology is also distinguished by not involving any additive or catalyst, readily available starting materials, wide range of substrate applicability, operational simplicity and simultaneously reassembling two C-N and two C-C bonds in one-step reaction.
View Article and Find Full Text PDFJ Org Chem
January 2025
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China.
In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through a radical difunctionalization of alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis and an open-flask atmosphere, and the reaction is highlighted with good yields and a broad reaction scope. Mechanism studies show that the reaction is initiated by a formal [4 + 2] cyclization of the sulfonyl radical in a regioselective manner.
View Article and Find Full Text PDFOrg Lett
December 2024
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China.
In this work, the annulation of acyl nitrene with alkynes is reported under photoredox/iron dual-catalysis for the synthesis of a series of isoquninalin-2-ones. The reaction is featured with a high reaction regioselectivity and good reaction generality. In particular, the resulting isoquinalin-2-ones could be structurally elaborated into several biologically interesting scaffolds.
View Article and Find Full Text PDFOrg Lett
December 2024
Department of Chemical Sciences, Tezpur University, Napaam, Sonitpur, Assam, India 784028.
We herein report the serendipitous discovery of the interrupted Plancher rearrangement initiated by an HFIP-promoted dearomative epoxide-indole cyclization, unlocking a new blueprint to the formal C3 umpolung reactivity of indoles. This rapid complexity generating cascade process paves the way toward a new class of fused-bridged indolines in high yields and under full regio- and diastereocontrol. The reaction is amenable to a wide range of substituents in the starting materials.
View Article and Find Full Text PDFCommun Chem
November 2024
College of Pharmacy and Medicinal Research Center (MRC) Chungbuk National University, Cheongju, 28160, Republic of Korea.
Pyridazine derivatives hold significant interest due to their broad applications in pharmaceuticals and materials science, where they serve as valuable scaffolds for bioactive compounds and functional materials. Here, we report a formal [4 + 2] reaction for the synthesis of 5'-sulfonyl-4'-aryl-3-cyano substituted pyridazine compounds from the reaction between vinylogous enaminonitriles and sulfonyl hydrazides. The key features of our pyridazine synthesis include the transamidation of vinylogous enaminonitriles with sulfonyl hydrazide, radical sulfonylation of the resulting intermediate, and subsequent 6-endo-trig radical cyclization.
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