A Dimroth rearrangement of pyrimidine nucleosides

Authors
Loakes, D Brown, DM Salisbury, SA
Citation
D. Loakes et al., A Dimroth rearrangement of pyrimidine nucleosides, J CHEM S P1, (10), 1999, pp. 1333-1337
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
10
Year of publication
1999
Pages
1333 - 1337
Database
ISI
SICI code
0300-922X(19990521):10<1333:ADROPN>2.0.ZU;2-B
Abstract
N-4-Acylamino-2'-deoxycytidine derivatives, 4a-c, undergo acid-promoted cyc lisation to give [1,2,4]triazolo-[4,3-c]pyrimidin-5(6H)-ones, 5a-c, in the presence of pyridinium chloride. This reaction has been demonstrated for a series of analogues. Treatment of the cyclised products in basic media give s rise to a novel Dimroth-type rearrangement leading to [1,2,4]triazolo[1,5 -c]pyrimidin-5(6H)-ones, 7a-c. The crystal structure of one such product, 1 5, was confirmed by X-ray analysis.