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Reactions of HDDA Benzynes with C,N-Diarylimines (ArCH=NAr').

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.

SUBMITTER: Arora S

PROVIDER: S-EPMC7990319 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Reactions of HDDA Benzynes with C,N-Diarylimines (ArCH=NAr').

Arora Sahil S Sneddon Dorian S DS Hoye Thomas R TR

European journal of organic chemistry 20200213 16

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-dihyd ...[more]

PMID: 33776554

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