1207-85-8Relevant academic research and scientific papers
Ylides of Heterocycles. VII. . I-, N-, P- and S-Ylides of Pyrimidones
Habib, Nargues Samuel,Kappe, Thomas
, p. 385 - 388 (2007/10/02)
The reaction of pyrimidone derivatives 1a-d with iodosobenzene prepared in situ from diacetoxyiodobenzene or dichloroiodobenzene afforded the iodonium-ylides 2a-d in good yields.Their thermal rearrangement produced 5-iodo-4-phenoxy-pyrimidin-6(1H)-ones 3a-c.Reductive deiodination of 3 gave the corresponding 4-phenoxypyrimidin-6(1H)-ones 4a-c.Acid catalized treatment of the iodonium-ylides 2a-d with nucleophiles such as pyridine, nicotinamide, isoquinoline, or triphenylphosphine produced the corresponding N- or P-ylides 7, 8, 9, and 10, respectively.The thiophanium-ylides 11a,c were obtained from the iodonium-ylides 2 without the use of a catalyst.The pyridinium-ylides 7 have also been prepared from the 5-halopyrimidones 5 or 6 which in turn could be obtained from the reactive iodonium-ylides 2 with hydrochloric or hydrobromic acid, respectively.
