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

Sahil Arora; Dorian S. Sneddon; Thomas R. Hoye

doi:10.1002/ejoc.201901855

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

Sahil Arora, Dorian S. Sneddon, Thomas R. Hoye

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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)
Pages (from-to)	2379-2383
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.201901855
State	Published - May 3 2020

Bibliographical note

Funding Information:
The U.S. Department of Health and Human Services, National Institutes of General Medical Sciences (R35 GM127097) supported this research. Some NMR spectroscopic data were obtained using an instrument funded through the NIH Shared Instrumentation Grant program (S10OD011952). Mass spectrometry was performed in the Analytical Biochemistry Shared Resource of the Masonic Cancer Center at the University of Minnesota, funded in part by a Cancer Center Support Grant (CA‐77598).

Funding Information:
The U.S. Department of Health and Human Services, National Institutes of General Medical Sciences (R35 GM127097) supported this research. Some NMR spectroscopic data were obtained using an instrument funded through the NIH Shared Instrumentation Grant program (S10OD011952). Mass spectrometry was performed in the Analytical Biochemistry Shared Resource of the Masonic Cancer Center at the University of Minnesota, funded in part by a Cancer Center Support Grant (CA-77598).

Publisher Copyright:
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Acridines
Azoquinone methides
Benzazetidines
Dihydroacridines
HDDA-benzynes

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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.",

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

Abstract

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Keywords

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