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Synthesis of β-nitropyrroles from amino sugars and nitroacetone

AuthorsChiara, José Luis ; Gómez-Sánchez, Antonio; Hidalgo, Francisco J. ; Yruela Guerrero, Inmaculada
Issue Date1-Jun-1989
CitationCarbohydrate Research 188: 55-62 (1989)
AbstractReactions of 2-amino-2-deoxy-d-glucose and 1-amino-1-deoxy-d-fructose with nitroacetone produced 2-methyl-3-nitro-5-(d-arabino-tetritol-1-yl)pyrrole (7) and 2-methyl-3-nitro-4-(d-arabino-tetritol-1-yl)pyrrole (11), respectively, in good yields. The reactions take place through the intermediacy of the unstable 2-nitrovinylamino sugars 5 and 13, the former compound having been isolated as its 1,3,4,6-tetra-O-acetyl derivative 9. Acetylation of 7 and 11 afforded the corresponding tetra-acetates 8 and 12. Periodate oxidation of 7 and 11 gave 5-methyl-4-nitro-2-pyrrolecarbaldehyde and 5-methyl-4-nitro-3-pyrrolecarbaldehyde, respectively, in good yields.
Description8 páginas.-- Trabajo presentado en el XIVth International Carbohydrate Symposium, Stockholm, Sweden, August 14–19, 1988.
Publisher version (URL)http://dx.doi.org/10.1016/0008-6215(89)84058-3
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