The Chemistry of Heterocyclic Compounds, Volume 63, The Naphthyridines
Chapter One
Primary Syntheses of 1,5-Naphthyridines
The primary synthesis of 1,5-naphthyridines may be accomplished by double
cyclization of appropriate aliphatic substrates; by cyclization of appropriately
substituted pyridines; by cyclocondensation of pyridine substrates with one or
more aliphatic synthons; or from other heterocyclic substrates by degradation,
rearrangement, or the like. Partially or fully reduced 1,5-naphthyridines are often
made by somewhat similar procedures; such cases are usually illustrated toward the
end of each subsection. Some reviews of naphthyridine chemistry contain material
on the primary synthesis of 1,5-naphthyridines.
1.1. FROM A SINGLE ALIPHATIC SUBSTRATE
This unlikely type of synthesis is represented by the reduction of 5,6-dimethyl-5,6-dinitrodecane-2,9-dione
(1) to give a mixture from which 2,4a,6,8a-tetramethyl-3,4,4a,7,8,8a-hexahydro-1,5-naphthyridine 1,5-dioxide
(2) was isolated via its p ... read full excerpt from The Chemistry of Heterocyclic Compounds ebook
