Abstract
Perkin condensations of arylglyoxylic acids with arylacetic acids, followed by the addition of alkylamine, yield diarylmaleimides in a one-pot procedure. The arylglyoxylic acids are obtained by arene acylation with ClCOCO 2Et and reduced with NaI and hypophosphorous acid to the arylacetic acids. With 2,7-di-tert-butyl-pyren-4-yl or chrysen-6-yl as the aryl, photocyclodehydrogenation of the diarylmaleimides yields substituted helicenes which can be reduced to stable anions. The helicenes combine bathochromically shifted absorption with hypsochromically shifted fluorescence with respect to their precursors.
Original language | English |
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Pages (from-to) | 1546-1549 |
Number of pages | 4 |
Journal | Organic letters |
Volume | 16 |
Issue number | 6 |
DOIs | |
Publication status | Published - 2014 Mar 21 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry