Reaction of 1-nitroso-2-naphthols with α-functionalized ketones and related compounds: the unexpected formation of decarbonylated 2-substituted naphtho[1,2-d][1,3]oxazoles.

Reactions between 1-nitroso-2-naphthols and α-functionalized ketones such as α-bromo-, α-chloro-, α-mesyloxy-, α-tosyloxy-, and α-hydroxy ketones under basic conditions delivered 2-substituted naphtho[1,2-d][1,3]oxazoles in a single synthetic operation. The product formation was accompanied by the unexpected loss of the C═O group from the α-functionalized ketones. With aryl bromides, allyl bromides, α-bromo diketones, α-bromo cyanides, α-bromoesters, and α-bromo ketoesters as substrates the formation of naphtho[1,2-d][1,3]oxazoles was also observed. The transformations were performed in 1,2-dichloroethane or acetonitrile under reflux and gave the corresponding naphthoxazoles with yields ranging between 52% and 85%.

Citation

Nayyef Aljaar, Chandi C Malakar, Jürgen Conrad, Wolfgang Frey, Uwe Beifuss. Reaction of 1-nitroso-2-naphthols with α-functionalized ketones and related compounds: the unexpected formation of decarbonylated 2-substituted naphtho[1,2-d][1,3]oxazoles. The Journal of organic chemistry. 2013 Jan 4;78(1):154-66

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PMID: 23181942

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