127743-67-3Relevant academic research and scientific papers
C-Nucleosides. 11. Synthesis of Quinoxaline C-Nucleosides through Condensation of 1,2-Diaminobenzenes with 6-Hydroxy-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dihydropyran-3-one
Maeba, Isamu,Kitaori, Kazuhiro,Itaya, Yoko,Ito, Chihiro
, p. 67 - 72 (2007/10/02)
The synthesis of 6- and 7-substituted-2-(β-D-ribofuranosyl)quinoxaline and 7- and 8-substituted-1-(β-D-ribofuranosyl)pyrroloquinoxaline from 6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dihydropyran-3-one (1) is described.Treatment of (1) with 1,2-diamino-4-chlorobenzene (2a) afford three compounds, the 6- and 7-chloroquinoxalines (3a) and (3b) and the 7-chloropyrroloquinoxaline (4a) in 23, 43, and 9percent yield, respectively.The position of the substituent in products (3a) and (3b) was determined by comparison of these 1H nmr spectra with thoseof the corresponding N-oxides (5a), (6a), and (5b), (6b), prepared by oxidation of compound (3a) and (3b) with m-chloroperbenzoic acid.The position of the substituent in (4a) was confirmed by 1H-13C long-range COSY experiment with corresponding deblocked pyrroloquinoxaline (4c).Treatment of compound (1) with 1,2-diamino-4-nitrobenzene (2b) afforded two compounds, the 6-nitroquinoxaline (3c) and the 8-nitropyrroloquinoxaline (4b).Deprotection of compounds (3a-c), (4a,b), (5a,b), and (6a,b) with methanolic sodium hydroxide afforded (3d-f), (4c,d), (5c,d), and (6c,d), respectively.
