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Synthesis of 3-(d-lyxofuranosyl)pyrazoles by trifluoroacetic acid-catalysed cyclodehydration of 3-(d-galacto-pentitol-1-yl)pyrazoles

✍ Scribed by Manuel Gómez-Guillén; José María Lassaletta Simon

Book ID
102995921
Publisher
Elsevier Science
Year
1991
Tongue
English
Weight
498 KB
Volume
211
Category
Article
ISSN
0008-6215

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✦ Synopsis

New 3-(D-gafucto-pentitol-I-yl)pyrazole derivatives have been obtained by the reaction of Dgalactose hydrazones and nitroalkenes. Cyclodehydration of the I-methyl-3-(D-galacto-pentitol-l-yl)pyrazoles in trifluoroacetic acid at room temperature afforded good yields of 3-(r-D-lyxofuranosyl)-l-methyl derivatives. A p anomer was obtained only for the 5-(p-tolyl) derivative.

📜 SIMILAR VOLUMES

Cyclodehydration of 3-(d-manno-pentitol-
Cyclodehydration of 3-(d-manno-pentitol-1-yl)pyrazoles: Synthesis of 3-(d-arabinofuranosyl)pyrazoles
✍ Manuel Gómez-guillén; José María Lassaletta-Simon; María Eloísa Martín-Zamora; I 📂 Article 📅 1990 🏛 Elsevier Science 🌐 English ⚖ 578 KB

Several 3-(D-manno-pentitol-I-yl)pyrazoles were cyclodehydrated by treatment with boiling aqueous 10% trifluoroacetic acid. The products were a&mixtures of 3-(D-arabinofuranosyI)pyrazoles in which the /3 anomer was the major component. The structures and configurations of these C-nucleoside analogue

1-Methyl(or phenyl)-5-(penta-O-acetyl-d-
1-Methyl(or phenyl)-5-(penta-O-acetyl-d-galacto-pentitol-1-yl)pyrazoles from the reactions of 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitro-d-galacto-hept-1-enitol with aldehyde methyl(or phenyl)hydrazones
✍ Manuel Gómez-Guillén; José María Lassaletta Simon 📂 Article 📅 1991 🏛 Elsevier Science 🌐 English ⚖ 887 KB

The title hept-I -enitol( 2) reacted with aldehyde methyl(or phenyl)hydrazones in refluxing methanol or butyl acetate to give I-methyl(or phenyl)-5-(penta-O-acetyl-~-~~u~u~f~~-pentitol-l-yl)pyrazoles in good (for I-methylpyrazoles) or moderate yields (for I-phenylpyrazolcs). The 0-deacetylated produ