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Diazomethane adds to plumbagin (la) yielding the indazolequinone 7 which, in the presence of sodium hydroxide, reacts to form nitrogen and the anion 4a. The latter reacts with excess juglone (lb) or juglone methyl ether (lc) forming isozeylanone (6a) and neozeylanone (6c) or their corresponding monomethyl ethers 6b and 6d, rsp. In a similar manner, the quinones 11a, 11c, and 15 originate by reaction of two molecules diazomethane with la via the indazoles 9 and 13, rsp.

zeitschrift für naturforschung b

Synthese von Neozeylanon und Isozeylanon und neue Reaktionen von Chinonen mit Diazomethan / Synthesis of Neozeylanone and Isozeylanone and New Reactions of Quinones with Diazomethane