[Synthesis of heteroaromatic N-beta-glycosides of N-acetylglucosamine under phase transfer conditions: II].
Regioselective N-beta-glucosamination of various unsubstituted or C4-, C5-, or C6-monosubstituted indolin-2-ones under phase transfer conditions was studied. The regioselectivity was unambiguously proved by (1)H NMR spectroscopy and X-ray analysis. The presence of a substituent at C7 of the aromatic ring leads to the formation of either a mixture of isomeric N-beta- and O-beta-D-glucosaminides or only oxazoline and/or 2-acetamidoglycal irrespective of the reaction conditions.
Kur'ianov
V O
VO
Vernadsky Tauric National University, pr. Akademika Vernadskogo 4, Simferopol, 95007 Crimea, Ukraine. vladimir@tnu.crimea.ua
Chupakhina
T A
TA
Shishkin
O V
OV
Shishkina
S V
SV
Chirva
V Ia
VIa
D000117:Acetylglucosamine / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D006027:Glycosides; D000117:Acetylglucosamine