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Report | Regular issue | Vol 20, No. 7, 1983, pp.1367-1371
Published online, 1st January, 1970
DOI: 10.3987/R-1983-07-1367
Mesoionic Six-membered Heterocycles, XVII. Cycloaddition of Benzyne to Mesoionic Pyrimidines

Thomas Kappe and Dietmar Pocivalnik

*Abteilung fur Angewandte, Organische Chimie, Institut fur Organische Chimie, Karl-Franzens Universitat, Heinrichstr. 28, A-8010 Graz, Austria


Benzyne (1) reacts with mesoionic pyrimidines (2a-e) yielding below 40 °C the primary cycloadducts 3a-e. At higher temperatures the isoquinolin-3-ones 4a-e are formed under the loss of phenyl isocyanate. Further addition of 1 to 4e yields the adduct 5, which is converted at 200 °C into the anthracene derivative 6.