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Reactions of HDDA Benzynes with C,N ‐Diarylimines (ArCH=NAr')
Author(s) -
Arora Sahil,
Sneddon Dorian S.,
Hoye Thomas R.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901855
Subject(s) - aryne , chemistry , cycloaddition , nucleophile , computational chemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
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 MnO 2 to provide structurally complex acridines.