Routes to N-vinyl-nitroimidazoles and N-vinyl-deazapurines

✍ Scribed by Russell Clayton; Christopher A. Ramsden

• Book ID: 102342903
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2004
• Tongue: English
• Weight: 154 KB
• Volume: 41
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570410508

✦ Synopsis

Abstract

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.