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Paper | Special issue | Vol 30, No. 2, 1990, pp.1121-1129
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S111
Synthesis of Some Quinones of Relevance to a Synthetic Approach to Amphimedine. Crystal Structure Determination of 1-Methylpyrido[4,3-g]quinoline-4,5,10-trione 5-N,N-Diisopropylhydrazone

Premji Meghami, Owen S. Mills, and John A. Joule*

*Department of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, U.K.


Tricyclic quinones are formed by the intramolecular strong acid catalyzed cycli-acylation of 2-(2-carboxyphenylcarbonyl)-1-methyl-4-pyridone and of 2-(4-methoxycarbonylpyridin-3-ylcarbonyl)-1-methyl-4-pyridone. Pyrido[4,3-g]quinoline-4,5,10-trione 6, thus produced, gives the 5-imine on reaction with ammonia; this imine reacts with lithium diisopropylamide to produce the 5-diisopropylhydrazone of 6.