The Dimroth Rearrangement of 6-Aminouracil Derivatives

The reaction of 6-amino-5-formyl (or acetyl) uracils (4) possessing a phenyl group at the 1-position with caustic alkali resulted in Dimroth rearrangement to give 6-anilino-5-formyl (or acetyl) uracils (5). This is the first example of Dimroth rearrangement observed in the uracil ring system. The pr...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1992/10/25, Vol.40(10), pp.2839-2841
Hauptverfasser:	HIROTA, Kosaku, NI, Pei-Zhou, SUZUKI, Akiyuki, TAKASU, Hideki, KITADE, Yukio, MAKI, Yoshifumi
Format:	Artikel
Sprache:	eng
Schlagworte:	6-aminouracil 6-anilinouracil alkaline hydrolysis Chemistry Dimroth rearrangement Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings molecular rearrangement Organic chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	The reaction of 6-amino-5-formyl (or acetyl) uracils (4) possessing a phenyl group at the 1-position with caustic alkali resulted in Dimroth rearrangement to give 6-anilino-5-formyl (or acetyl) uracils (5). This is the first example of Dimroth rearrangement observed in the uracil ring system. The presence of both the N1-phenyl group and the 5-formyl (or acetyl) group on the uracil ring is requisite for the occurrence of the rearrangement.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.40.2839