508235-09-4Relevant academic research and scientific papers
N-vinyl-nitroimidazole cycloadditions: Potential routes to nucleoside analogues
Clayton, Russell,Ramsden, Christopher A.
, p. 2695 - 2700 (2007/10/03)
Cycloaddition reactions of 4-nitro- and 5-nitro-1-vinylimidazoles have been investigated. The cycloadducts obtained are potential intermediates for synthesis of purine nucleoside analogues via reduction to the corresponding aminoimidazoles. A byproduct obtained using benzonitrile oxide as 1,3-dipolarophile has been identified as a novel tricyclic isomer 12 of the cycloadduct 11. Georg Thieme Verlag Stuttgart.
Routes to N-vinyl-nitroimidazoles and N-vinyl-deazapurines
Clayton, Russell,Ramsden, Christopher A.
, p. 701 - 705 (2007/10/03)
The preparations of 4- and 5-nitro-1-vinylimidazole (2 and 7) are described. Selective reduction of the nitro group using Fe/dil HCl is achieved for the 4-nitro derivative but this is not effective when ethoxymethylenemalononitrile is used to trap the amine. For 5-nitroimidazole studies the N-vinyl substituent is kept masked as a 2-chloroethyl group, which remains unchanged during catalytic reduction of the nitro function (Pd/C), and is revealed by HCl elimination at a later stage. In this way, the 1-deazapurine 13 and the tricyclic derivative 14 have been prepared.
