Diversity of rearrangement of 3-substituted 5-carbamoyl-1-phenyluracil derivatives

Authors
Sajiki, H Fujita, Y Niimoto, I Hirota, K
Citation
H. Sajiki et al., Diversity of rearrangement of 3-substituted 5-carbamoyl-1-phenyluracil derivatives, HETEROCYCLE, 50(1), 1999, pp. 385-392
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
50
Issue
1
Year of publication
1999
Pages
385 - 392
Database
ISI
SICI code
0385-5414(19990101)50:1<385:DORO35>2.0.ZU;2-K
Abstract
Treatment of 3-substituted 5-carbamoyl-1-phenyluracil derivatives (lac) wit h NaH afforded 5-(N-substituted carbamoyl)-1-phenyluracil derivatives (2a-c ) via rearrangement involving the rare C(2)-N(3) bond cleavage of a uracil ring system. Upon reaction of 5-N-methylcarbamoyl-1-phenyluracil derivative s (4a and 4b) and 3-methyl-1-phenyl-5-thiocarbamoyluracil (6) with NaH, 5-( anilino-methylene)barbituric acid derivatives (5a, b and 7) formed, respect ively, via rearrangement involving the N(1)-C(2) bond cleavage.