Synthesis of 9-Phenylacridines via Ortho-Lithiation-Cyclization Sequence

Chemistry of Heterocyclic Compounds 2015
Artis Kinēns, Toms Kalniņs, Edgars Sūna

Herein, we describe a previously unreported formation of acridines from triarylcarbinols under acidic conditions. Thus, treatment of tertiary alcs. with conc. aq. HCl in glacial AcOH at 90° provided 9-phenylacridines in 91-92% yield. The starting tertiary alcs. were prepd. by double addn. of ortho-lithiated pivaloyl anilines to benzoyl chloride in 76 and 68% yield, resp. Overall, the two-step ortho-lithiation cyclization sequence constitutes a convenient approach to 9-phenylacridines.

Keywords
acridine oxazine tertiary alcohol cyclization ortho-lithiation
DOI
10.1007/s10593-014-1616-y
Hyperlink
http://link.springer.com/article/10.1007%2Fs10593-014-1616-y

Kinēns, A., Kalniņs, T., Sūna, E. Synthesis of 9-Phenylacridines via Ortho-Lithiation-Cyclization Sequence. Chemistry of Heterocyclic Compounds, 2015, Vol.50, Iss.10, pp.1501-1505. e-ISSN 1573-8353. Available from: doi:10.1007/s10593-014-1616-y

Publication language
English (en)