Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes

Ondertitel:new synthesis of naphtho[2,1-d]oxazole compounds

Treatment of 3-substituted 2-amino-1,4-naphthoquinones 3 with an aldehyde in a solution of hydrobromic acid in acetic acid led to 2,4-disubstituted naphtho[2,1-d]oxazol-5-ols. The outcome of this simple conversion is even more remarkable in view of the very similar reactions reported in literature, which all give rise to completely different products. Furthermore, the acquired naphthoxazoles 511 could be oxidatively ring opened by means of PIFA or CAN into a series of N-acylated 2-amino-1,4-naphthoquinones. A synthetic pathway towards 2-substituted naphtho[2,3-d]oxazole-4,9-diones was also disclosed as the outcome of CAN mediated oxidation of a 4-chloronaphtho[2,1-d]oxazol-5-ol.

Jaar van publicatie:2011

Trefwoorden:A1 Journal article

BOF-keylabel:ja

BOF-publication weight:1

CSS-citation score:1

Authors from:Higher Education

Toegankelijkheid:Closed