TiCl4‐Mediated Dealkylative Cyclization of Arylidene‐azol‐ones

A new general approach for the synthesis of azolo[4,5‐b]quinolines via dealkylative TiCl4‐mediated cyclization of 2‐dialkylamino‐arylidene‐azol‐ones upon heating in dichloroethane is found. The reaction scope and limitations are established, showing that at least two different heterocyclic cores cou...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2022-12, Vol.7 (45), p.n/a
Main Authors: Zaitseva, Elvira R., Ivanov, Dmitrii S., Sokolov, Anatolii I., Mikhaylov, Andrey A., Baleeva, Nadezhda S., Korlyukov, Alexander A., Myasnyanko, Ivan N., Smirnov, Alexander Y., Baranov, Mikhail S.
Format: Article
Language:English
Subjects:
Amination
Cyclization
Imidazoquinolones
Thiazoloquinolinones
TiCl4
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Summary:A new general approach for the synthesis of azolo[4,5‐b]quinolines via dealkylative TiCl4‐mediated cyclization of 2‐dialkylamino‐arylidene‐azol‐ones upon heating in dichloroethane is found. The reaction scope and limitations are established, showing that at least two different heterocyclic cores could be obtained. Dozen products were obtained in moderate to good yields (22–64 %). Reaction of various ortho‐dialkylaminoarylidene‐azol‐ones with TiCl4 has been studied. Novel and non‐trivial approach to azolo[4,5‐b]quinolines with fair generality is proposed.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202203294