Alkoxy- and Aryloxy-1,8-Naphthyridines

Most available information on these ethers has been covered already. 

Note Alkoxy/aryloxy-l,8-naphthyridines have been made by primary synthesis (see Chapter 22), by alcoholysis/phenolysis of halogeno-l,8-naphthyridines (see Section 24.2), by alkylation of 1,8-naphthyridinones (see Section 25.1.2), and by two minor procedures illustrated here. 

7-Diazido-3-phenyl-l,8-naphthyridine (24, R = N3) gave selectively 2-azido-7-methoxy-3-phenyl-l,8-naphthyridine (24, R = OMe) (MeONa/MeOH, reflux 73%).285 

A substrate formulated as the benzylidene derivative (25) has been reported to afford the epoxy derivative (26) (H202, HO 75%).1102 

Note The hydrolysis of alkoxy-l,8-naphthyridines to 1,8-naphthyridinones has been exemplified in Section 25.1.1. No other reactions appear to have been reported. 

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