Relatively unstable cyclic imines, generated in situ from their corresponding alicyclic amines via oxidation of their lithium amides with simple ketone oxidants, engage aryllithium compounds containing a leaving group on an -methylene functionality to provide polycyclic isoindolines in a single operation. The scope of this transformation includes pyrrolidine, piperidine, azepane, azocane, and piperazines.
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http://dx.doi.org/10.1021/acs.orglett.2c00018 | DOI Listing |
Pharmaceuticals (Basel)
August 2023
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
Novel analogs of quinoline and isoindoline containing various heterocycles, such as tetrazole, triazole, pyrazole, and pyridine, were synthesized and characterized using FT-IR, NMR, and mass spectroscopy, and their antioxidant and antidiabetic activities were investigated. The previously synthesized compound was utilized in conjugation with ketone-bearing tetrazole and isoindoline-1,3-dione to synthesize Schiff's bases and . Furthermore, hydrazide was treated with aryledines to provide pyrazoles -.
View Article and Find Full Text PDFJ Org Chem
February 2023
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw 01-224, Poland.
A palladium-catalyzed strategy for isoindole -oxide ring construction by C-H functionalization of aldonitrones is described. Our protocol is of general character, providing isoindole -oxides with a variety of functional groups, including very sterically congested products. Further transformations into spirocyclic isoindolines, isoindoles, or a polycyclic isoquinolinium salt have been demonstrated as well.
View Article and Find Full Text PDFOrg Lett
February 2022
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Relatively unstable cyclic imines, generated in situ from their corresponding alicyclic amines via oxidation of their lithium amides with simple ketone oxidants, engage aryllithium compounds containing a leaving group on an -methylene functionality to provide polycyclic isoindolines in a single operation. The scope of this transformation includes pyrrolidine, piperidine, azepane, azocane, and piperazines.
View Article and Find Full Text PDFChem Sci
December 2021
College of Chemistry and Chemical Engineering, Henan University Kaifeng 475004 China
Simultaneous deconstructive ring-opening and skeletal reconstruction of an inert, aromatic pyridinium ring is of great importance in synthetic communities. However, research in this area is still in its infancy. Here, a skeletal re-modeling strategy was developed to transform chalcone-based pyridinium salts into structurally intriguing polycyclic isoindolines through a dearomative ring-opening/ring-closing sequence.
View Article and Find Full Text PDFChirality
December 2021
Department of Chemistry, Columbia University, New York, NY, USA.
This review continues our interest in the intriguing reports of a variety of new racemic natural products (at least 11 in the past 4 years). These include the polyphenolic racemate galewone, the polycyclic prenylated acylphloroglucinol garcinielliptone; variecolortide, a combination of an anthraquinone and a isochinulin-type alkaloid; the isoindoline alkaloid irpexine, the new hybrid phenylproanoid asarone; colletopyandione an indolydenepyradione; the enantiomerically enriched (scalemic) neolignans, gardenifolins; and meroterpenoid pabmaragramin in addition to some marine lipids. We also present a recent biomimetic synthesis of the polyketide preuisolactone A; synthesis of the polyketide spiromamakone A, which also corrected the proposed structure of another metabolite as identical to spiromamakone A; and the melicolones A and B.
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