SYNTHESIS OF NEOZEYLANONE AND ISOZEYLANON E AND NEW REACTIONS OF QUINONES WITH DIAZOMETHANE

Diazomethane adds to plumbagin (1a) yielding the indazolequinone 7 whi ch, in the presence of sodium hydroxide, reacts to form nitrogen and t he anion 4a, The latter reacts with excess juglone (1b) or juglone met hyl ether (1c) forming isozeylanone (6a) and neozeylanone (6c) or thei r 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.