Synthesis and X-ray structures of unexpected 2-O-(5-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-5-yloxy)quinoxalines

• Published in: Journal of physical organic chemistry 2009-06, Vol.22 (6), p.585-592
• Main Authors: Jarmoumi, Chakir, Lakhrissi, Brahim, Mondieig, Denise, Négrier, Philippe, Léger, J. M., Massip, S., Lazar, Zhor, Benali, Bouziane, Massoui, Mohamed, Essassi, El Mokhtar
• Format: Article
• Language: English
• Subjects: glucosyl-quinoxalines; phase transition; Quinoxalinones; synthesis; water solubility; X-ray structure
• ISSN: 0894-3230; 1099-1395
• DOI: 10.1002/poc.1486

Reaction of 3‐methyl‐2(1H)‐quinoxalinone (4) and 2(1H)‐quinoxalinone (5) with 5,6‐anhydro‐1,2‐O‐isopropylidene‐ α‐D‐glucofuranose 6 gives the unexpected O‐glucoquinoxalines derivatives by the intermediary novel intramolecular rearrangement of 5,6‐anhydro‐1,2‐O‐isopropylidene‐α‐D‐glucofuranose to the corresponding 3,6‐anhydro form. The obtained O‐glucoquinoxalines 7,8 were identified by NMR spectroscopy. The X‐ray crystal structures have been determined at room temperature. Moreover, a solid–solid phase transition has been detected at 198.9 K for O‐glucoquinoxalines 7 and the structure of the low‐temperature phase has been solved at 188 K. Copyright © 2009 John Wiley & Sons, Ltd. Reaction of 3‐methyl‐2(1H)‐quinoxalinone (4) and 2(1H)‐quinoxalinone (5) with 5,6‐anhydro‐1,2‐O‐isopropylidenea‐D‐glucofuranose 6 gives the unexpected O‐glucoquinoxalines derivatives by the intermediary novel intramolecular rearrangement of 5,6‐anhydro‐1,2‐O‐isopropylidene‐a‐D‐glucofuranose to the corresponding 3,6‐anhydro form. The obtained O‐glucoquinoxalines 7,8 were identified by NMR spectroscopy. The X‐ray crystal structures have been determined at room temperature. Moreover, a solid‐solid phase transition has been detected at 198.9 K for O‐glucoquinoxalines 7 and the structure of the low‐temperature phase has been solved at 188 K.