Synthesis and X-ray structures of unexpected 2-O-(5-deoxy-1,2-O-isopropylidene-\alpha- D-glucofuranos-5-yloxy)quinoxalines - Archive ouverte HAL
Article Dans Une Revue Journal of Physical Organic Chemistry Année : 2009

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

Résumé

Reaction of 3-methyl-2(1H)-quinoxalinone (4) and 2(1H)-quinoxalinone (5) with 5,6-anhydro-1,2-O-isopropylidene\alpha- D-glucofuranose 6 gives the unexpected O-glucoquinoxalines derivatives by the intermediary novel intramolecular rearrangement of 5,6-anhydro-1,2-O-isopropylidene \alpha-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

Dates et versions

hal-00506118 , version 1 (27-07-2010)

Identifiants

Citer

Chakir Jarmoumi, Brahim Lakhrissi, Denise Mondieig, Philippe Négrier, Jean-Michel Léger, et al.. Synthesis and X-ray structures of unexpected 2-O-(5-deoxy-1,2-O-isopropylidene-\alpha- D-glucofuranos-5-yloxy)quinoxalines. Journal of Physical Organic Chemistry, 2009, 22 (6), pp.585-592. ⟨10.1002/poc.1486⟩. ⟨hal-00506118⟩

Collections

CNRS LOMA
66 Consultations
0 Téléchargements

Altmetric

Partager

More