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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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 609–618, March, 2008.
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Paponov, B.V., Shishkin, O.V., Shishkina, S.V. et al. Dimerization of 3-(2-aryl-2-oxoethylidene)oxindoles. Russ Chem Bull 57, 622–631 (2008). https://doi.org/10.1007/s11172-008-0098-4
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DOI: https://doi.org/10.1007/s11172-008-0098-4