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Oxazoles formation during O ‐alkylation of isonitroso‐naphthols. X‐ray structure of [1,2]naphthoquinone 1‐[ O ‐(4‐ tert ‐butyl‐benzyl)‐oxime] and 2‐(4‐ tert ‐butyl‐phenyl)napth[1,2‐ d ]oxazole
Author(s) -
Astolfi Paola,
Carloni Patricia,
Castagna Riccardo,
Greci Lucedio,
Stipa Pierluigi,
Rizzoli Corrado
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410618
Subject(s) - chemistry , triethylamine , oxime , nitroso , alkylation , aryl , medicinal chemistry , x ray , 1,4 naphthoquinone , quinone , organic chemistry , catalysis , alkyl , physics , quantum mechanics
1‐Nitroso‐2‐naphthol and 2‐nitroso‐1‐naphthol, both in the isonitroso form, react with benzyl bromides in THF and in the presence of triethylamine affording, in low yields, the corresponding O ‐benzyl oximes and 2‐aryl naphthoxazoles in a 1:1 ratio, approximately. The structures of O ‐benzyl oximes and naphthoxazoles isolated have been determined by X‐ray analysis.