A Multi‐component Reaction of Hexafluoro‐1,4‐naphthoquinone with N‐Heterocycles and Active Methylene Compounds: A Straightforward Approach to Polyfluorinated Zwitterions

A Multi‐component Reaction of Hexafluoro‐1,4‐naphthoquinone with N‐Heterocycles and Active Methylene Compounds: A Straightforward Approach to Polyfluorinated Zwitterions Full article

Journal

Asian Journal of Organic Chemistry
ISSN: 2193-5815 , E-ISSN: 2193-5807

Output data

Year: 2025, Article number : e202400751, Pages count : DOI: 10.1002/ajoc.202400751

Authors

Kudryavtseva Ekaterina ¹ , Lichitsky Boris ¹ , Tretyakov Evgeny ¹

Affiliations

1	Zelinsky Institute of Organic Chemistry RAS Laboratory of heterocyclic compounds named after academician A.E.Chichibabin Leninsky Prospekt, 47 119991 Moscow RUSSIAN FEDERATION

For the first time, multi-component condensation of hexafluoro-1,4-naphthoquinone with nitrogen-containing heterocycles and active methylene compounds was studied. It was shown that the aforementioned process leads to the formation of a previously undescribed type of zwitterionic derivatives. Based on the results, a general one-step method for preparation of polyfluorinated pyridine-containing betaines was developed. Advantages of the proposed synthetic protocol are atom economy, readily available starting materials and simple isolation of target products without chromatographic purification. The obtained zwitterions were utilized as precursors for the preparation of new fluorinated polycyclic compounds: pyrido[1,2-a]indole-6,11-diones and naphtho[2,3-b]furan-4,9-diones.

Kudryavtseva E. , Lichitsky B. , Tretyakov E.
A Multi‐component Reaction of Hexafluoro‐1,4‐naphthoquinone with N‐Heterocycles and Active Methylene Compounds: A Straightforward Approach to Polyfluorinated Zwitterions
Asian Journal of Organic Chemistry. 2025. e202400751 . DOI: 10.1002/ajoc.202400751 WOS OpenAlex

Web of science:	WOS:001422781400001
OpenAlex:	W4406902309

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