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Abstract
6-Aroyl-7-arylindolo[3,4-jk]phenanthridin-5(4H)-ones (2a–i) were synthesized by heating 3-(2-aryl-2-oxoethylidene)-2,3-dihydroindol-2-ones (1a–i) in DMF. Compounds 2a–i are formed via the dimerization of two molecules of unsaturated ketones 1a–i proceeding as the [2+4] cycloaddition through the formation of intermediate spiro adducts. The further Pfitzinger rearrangement, decarboxylation, and heteroaromatization afford compounds 2a–i. The structures of the reaction products were established by spectroscopic methods and X-ray diffraction.
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