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DOI: 10.1055/s-2007-965931
Sodium Hydride Mediated Cascade Reaction towards the Synthesis of 1,5-Disubstituted Uracil from Cyanamides Derived from Baylis-Hillman Adducts [1]
Publikationsverlauf
Publikationsdatum:
13. Februar 2007 (online)
Abstract
The substituted cyanamides generated from Baylis-Hillman adducts afford 1,5-disubstituted uracils via a sodium hydride induced cascade reaction involving sequential intramolecular attack of the hydroxy group on the nitrile group, cyclization of the resulting ureide with the ester moiety, and rearrangement of the exocyclic double bond.
Key words
heterocycles - ring closure - 1,5-disubstituted uracil - cascade reaction - Baylis-Hillman reaction
CDRI communication number: 7125.
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References
CDRI communication number: 7125.
10Crystal data of compound 5c: C19H20N2O3, M = 324.37, monoclinic (solvent: CHCl3), P21/n, a = 12.626 (2), b = 9.117 (1), c = 14.631 (1) Å, β = 90.81 (1)°, V = 1684.0(3) Å3, Z = 4, D
c
= 1.279 (2) g·cm-3,
µ (Mo-Kα) = 0.09 mm-1, F(000) = 688.0, colorless block, 0.225 × 0.20 × 0.175 mm, 4097 reflections measured
(R
int = 0.0234), 2972 unique, wR
2 = 0.1277, conventional R = 0.0497 on F
2 values of 1573 reflections with I > 2σ(I), (Δ/σ) max = 000), S = 0.962 for all data and 219 parameters. Unit cell determination and intensity data
collection (2θ = 50°) were performed on a Bruker P4 diffractometer at 293 (2) K. Structure
solutions by direct methods and refinements were by full-matrix least-squares methods
on F
2. Programs: XSCANS (Siemens Analytical X-ray Instrument Inc.: Madison, WI, USA, 1996)
for data collection and data processing; SHELXTL-NT (Bruker AXS Inc.: Madison, Wisconsin,
USA, 1997) for structure determination, refinements, and molecular graphics. Further
details of the crystal structure investigation can be obtained from the Cambridge
Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK (CCDC deposition
no. 629774). (For queries related to the X-ray structure write to maulik_prakas@yahoo.com).