Abstract
o-Benzynes can be utilized to construct heterocyclic motifs using various nucleophilic and cycloaddition trapping reactions. Acridines have been synthesized by capture of C,N-diarylimines with benzynes generated by classical methods (i.e., from ortho-elimination of precursor arene compounds), although in poor yields. We report here that these imines can be trapped by benzynes generated by the hexadehydro-Diels–Alder (HDDA) reaction in an efficient manner to produce 1,4-dihydroacridine products. These dihydroacridines were subsequently aromatized using MnO2 to provide structurally complex acridines.
Original language | English (US) |
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Pages (from-to) | 2379-2383 |
Number of pages | 5 |
Journal | European Journal of Organic Chemistry |
Volume | 2020 |
Issue number | 16 |
DOIs | |
State | Published - May 3 2020 |
Bibliographical note
Publisher Copyright:© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords
- Acridines
- Azoquinone methides
- Benzazetidines
- Dihydroacridines
- HDDA-benzynes