Preparation of Pyrimidine-N-oxides by Condensation of Functionalized Enamides with Hydroxylamine Hydrochloride

Autor:	Tilman Lechel, Giaime Rancan, Hans-Ulrich Reissig, Reinhold Zimmer, Mrinal K. Bera
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Acetic acid chemistry.chemical_compound Hydroxylamine chemistry Pyrimidine Aryl Organic Chemistry Condensation Organic chemistry Hydroxylamine Hydrochloride Alkyl
Zdroj:	Synlett. 2010:1793-1796
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0030-1258088
Popis:	β-Alkoxy-β-ketoenamides and hydroxylamine hydrochloride smoothly provide pyrimidine-N-oxides under very mild conditions. Alkyl, aryl, and heteroaryl substituents are compatible with this new method. By treatment with acetic acid anhydride these pyrimidine-N-oxides undergo a rearrangement furnishing highly functionalized 6-acetoxymethyl-substituted pyrimidine derivatives in good yields. Our method, which is based on a three-component reaction of alkoxyallenes, nitriles, and carboxylic acids, therefore constitutes a highly flexible route to densely substituted pyrimidine derivatives.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d9dd74e6ce8a44c7ad3c7d9ddc364504 https://doi.org/10.1055/s-0030-1258088 Zobrazit plný text záznamu