Regioselective [3+2] cycloaddition of chalcones with a sugar azide: easy access to 1-(5-deoxy-D-xylofuranos-5-yl)-4,5-disubstituted-1H-1,2,3-triazoles.
[3+2] Cycloaddition of 5-azido-5-deoxy-1,2-O-isopropylidene-alpha-d-xylofuranose with 1,3-diphenyl-prop-3-enones, followed by oxidation of the intermediate triazolines in a tandem manner, led to the regioselective formation of 4-benzoyl-1-(5-deoxy-1,2-O-isopropylidene-alpha-d-xylofuranos-5-yl)-5-phenyl-1H-1,2,3-triazoles in moderate to good yields.
Singh
Nimisha
N
Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow 226 001, CSIR, India.
Pandey
S K
SK
Tripathi
Rama P
RP
D001386:Azides / Q000737:chemistry*; D047188:Chalcones / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014994:Xylose / Q000031:analogs & derivatives* / Q000737:chemistry
D001386:Azides; D047188:Chalcones; D014230:Triazoles; D014994:Xylose