Naphthyridinecarbonitriles, Carbaldehydes, and Ketones

Available information on these entities is summarized here. 

Preparation. Most such nitriles have been made by primary synthesis (see Chapter 8). However, 1,6-naphthyridine A-oxides undergo oxidative cyana-tion, as illustrated here. 1,6-Naphthyridine 1-oxide (24) gave 1,6-naphthyr-idine-2-carbonitrile 1-oxide (25) [substrate, K3Fe(CN)6, KCN, H20, 0°C, 3 h 58%] l,6-naphthyridme-5-carbonitrile 6-oxide (29%) and a separable mixture of l,6-naphthyridine-2-carbonitrile 1,6-dioxide (30%), 1,6-naphthyridine 5-carbonitrile 1,6-dioxide (14%), and l,6-naphthyridine-2,5-dicarbomtrile 

Reactions. These nitriles have been hydrolyzed to carboxylic acids or carboxamides (see Sections 14.1.1 and 14.3, respectively. 

Preparation. Both types of derivative have been prepared by primary synthesis (see Chapter 8) or by N-acylation (see Section 13.2.2). 

Reactions. A case of C-deacylation appears to be the only reported reaction of these derivatives. A Ru complex has been made.1262 3-Acetyl-l,5-dibenzyl- 

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