Fluorinated cyclopropanes for 2-heterosubstituted electron-rich indolizine synthesis

Fluorinated cyclopropanes for 2-heterosubstituted electron-rich indolizine synthesis Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2025, Volume: 23, Pages: 6616-6624 Pages count : 9 DOI: 10.1039/d5ob00628g

Authors

Bobrova Angelina Yu. ¹ , Novikov Maxim A. ¹ , Burykina Julia V. ¹ , Trainov Konstantin P. ¹ , Tomilov Yury V. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia

Fluorinated cyclopropanes were proven to be valuable precursors for a wide range of 2-heterosubstituted electron-rich indolizines, hardly accessible by other methods due to their instability. Copper(I) activation of C–X bonds permits disubstituted fluorocyclopropanes to undergo ring opening in the presence of pyridines, yielding (2-fluoroallyl)pyridinium salts. These intermediates were found to undergo base-promoted cyclization, either retaining the fluorine atom or undergoing intermolecular fluorine substitution with additional NuH, producing two- or three-component-derived 2-F,N,S,O-subtituted indolizines. This strategy allows 2-heterosubsituted indolizines with different 1,3-substitutition and nucleophilic parts to be prepared, including ones with functional groups capable of coupling with biologically relevant structures. The 2-heteroindolizines obtained exhibit blue-light emission with high intensity in DMSO, good Stokes shift and notable quantum yields.

Bobrova A.Y. , Novikov M.A. , Burykina J.V. , Trainov K.P. , Tomilov Y.V.
Fluorinated cyclopropanes for 2-heterosubstituted electron-rich indolizine synthesis
Organic & Biomolecular Chemistry. 2025. V.23. P.6616-6624. DOI: 10.1039/d5ob00628g WOS Scopus OpenAlex

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