By Desmond J. Brown, Jonathan A. Ellman, Edward C. Taylor
A quantity within the Chemistry of Heterocyclic Compounds sequence, this publication offers a precis of the chemistry of every of the six naphthyridine structures besides tables of recognized uncomplicated derivatives with unique references. all of the six naphthyridine structures are defined in necessary element and assurance contains: fundamental artificial equipment from non-naphthyridine substrates; Chemistry and houses of the father or mother heterocycle and its uncomplicated alkyl derivatives; Formation and reactions of halogeno derivatives; formation and reactions of hydroxy, oxo, alkoxy, and comparable derivatives.
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Additional info for The Chemistry of Heterocyclic Compounds, The Naphthyridines
233 The yield was lower than that obtained by using neat phosphoryl chloride (see preceding list of examples), but a sealedtube reaction was avoided by this procedure. Cl N N Cl (21) 1,5-Naphthyridin-2 (1H)-one gave 2-chloro-1,5-naphthyridine (PCl5, POCl3, reﬂux, 4 h: 70%;262 again a lower yield than when neat POCl3 was used). 3. By the Meissenheimer Reaction on 1,5-Naphthyridine N-Oxides The conversions of 1,5-naphthyridine N-oxides into C-halogeno-1,5-naphthyridines by the Meissenheimer reaction (POCl3 or POBr3) or a related reaction (Br2 in Ac2O) both suffer from the fact that two or more products are usually formed in each case.
By Direct Halogenation This route has occasionally been followed to make both nuclear and extranuclear halogeno-1,5-naphthyridines. Some examples follow. J. Brown Copyright # 2008 John Wiley & Sons, Inc. 3. 2. By Halogenolysis of 1,5-Naphthyridinones or the Like The conversion of a tautomeric 1,5-naphthyridinone into the corresponding chloro- or bromo-1,5-naphthyridine is usually done by heating for several hours with neat phosphoryl chloride or phosphoryl bromide, respectively. A mixture of phosphoryl chloride and phosphorus pentachloride has been used for a few difﬁcult cases.
A mixture of phosphoryl chloride and phosphorus pentachloride has been used for a few difﬁcult cases. In addition, exceptional reactions have been reported in which a nontautomeric N-alkyl-1,5-naphthyridinone or a hydroxymethyl-1,5-naphthyridine was used successfully as substrate. The following examples illustrate the foregoing possibilities. 818 Cl Cl N N NO2 N Br (15) N NO2 N N (16) (17) Cl Using Phosphorus Pentachloride in Phosphoryl Chloride Note: This mixture has been used for chlorolyses that were perceived as difﬁcult, but phosphorus pentachloride can introduce complications.