55649-78-0Relevant academic research and scientific papers
Hydrophilically functionalized pyrazoles from sugars
Oikawa, Nobuhiro,Mueller, Christoph,Kunz, Markwart,Lichtenthaler, Frieder W.
, p. 269 - 279 (2007/10/03)
An effective and convenient protocol has been developed for the conversion of D-glucose and 6-O-α-D-glucopyranosyl-D-fructose (palatinose, isomaltulose) into 5-[(1'S)-1','2/-dihydroxyethyl]-1-phenylpyrazole-3-carboxaldehyde (4) and 5-[(1'S)-2-(α-D-glucopyranosyloxy)-1-hydroxethyl])-1-phenylpyrazole-3 -carboxaldehyde (5), key steps being the acetic anhydride-promoted dehydrative cyclization of the respective phenylosazones, and subsequent liberation of the N-acetylphenylhydrazone-blocked aldehyde function. Exploitation of the ensuing chemistry of 4 and 5 led to a variety of pyrazole building blocks with a diverse level of hydrophilic substituents (hydroxymethyl, dihydroxyethyl or glucosyl residues) and useful functional groups, such as chloro, cyano, aminomethyl, vinyl and acryloyl moieties.
A CONTRIBUTION TO THE CHEMISTRY OF PYRAZOLE-TYPE DIANHYDROPHENYLOSAZONES
Somogyi, Laszlo
, p. 71 - 76 (2007/10/02)
3,4,5,6-Tetra-O-acetyl-D-lyxo-hexosulose 1-acetylphenylhydrazone 2-phenylhydrazone (10) was transformed into 5-(D-glycero-1,2-diacetoxyethyl)-3-formyl-1-phenylpyrazole acetylphenylhydrazone (D-4, n=3) in boiling acetic anhydride containing anhydrous sodiu
