Reactions of 1,8-Naphthyridinones and the Like

The halogenolysis of 1,6-naphthyridinones and extranuclear hydroxy-1,6-naphthyridines has been covered in Section 10.1.2. Other reactions are illustrated in the following classified examples. 

Note This is usually done via the corresponding halogeno derivative, but direct reduction can give a nuclear reduced product. 

6-Dibenzyl-4-hydroxy-7-methyl-1,6-naphthyridine-2,5( 17/,677)-dione (13) gave 

6-dibenzyl-4-hydroxy-7-methyl-5,6-dihydro-1,6-naphthyridin-2( 1 //)-one (14) (B2H6, THF 79%).950 o 

Note Alkylation or arylation of any tautomeric 1,6-naphthyridinone probably affords a mixture of O- and /V-derivatives, but the latter usually predominates. 

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