In:
QSAR & Combinatorial Science, Wiley, Vol. 25, No. 8-9 ( 2006-09), p. 753-760
Abstract:
This paper describes a novel fluorous synthesis of fluorinated uracils 4. In this new protocol, fluorous alcohols 1 , which are used as fluorous tags, are acetylated to yield acetates 2 , which in turn are treated with a base to form their enolates. These are then reacted with fluorinated nitriles to furnish tagged β‐enamino esters 3. Although this condensation step had been performed easily in previous solution and solid‐phase syntheses, it proved to be very elusive in the fluorous version. Meticulous control of the reaction conditions was thus essential in order to achieve satisfactory yields of β‐enamino esters 3. The final treatment of compounds 3 with isocyanates or isothiocyanates efficiently afforded uracils 4 with concomitant elimination of the fluorous tag, thereby facilitating the preparation of a small library of these derivatives.
Type of Medium:
Online Resource
ISSN:
1611-020X
,
1611-0218
DOI:
10.1002/qsar.v25:8/9
DOI:
10.1002/qsar.200640057
Language:
English
Publisher:
Wiley
Publication Date:
2006
detail.hit.zdb_id:
2537668-8
detail.hit.zdb_id:
2010584-8
SSG:
12
SSG:
15,3
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