Publication
Title
Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes : new synthesis of naphtho[2,1-d]oxazole compounds
Author
Abstract
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.
Language
English
Source (journal)
Tetrahedron. - Oxford
Publication
Oxford : 2011
ISSN
0040-4020
Volume/pages
67:2(2011), p. 512-517
ISI
000286499000029
Full text (Publisher's DOI)
Full text (publisher's version - intranet only)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 09.04.2011
Last edited 04.11.2017
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