Reaction of 1-Nitroso-2-napthols with α-Functionalized Ketones and Related Compounds: The Unexpected Formation of Decarbonylated 2- Substituted Napththo[1,2-d][1,3]oxazoles

Publikations-Art

Zeitschriftenbeitrag (peer-reviewed)

Autoren

Aljaar, N.; Malakar, C. C.; Conrad, J.; Frey, W.; Beifuss, U.

Erscheinungsjahr

2013

Veröffentlicht in

J. Org. Chem.

Band/Volume

78/

DOI

10.1021/jo3022956

Seite (von - bis)

154-166

Reactions between 1-nitroso-2-naphthols and α-functionalized ketones like 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%.