Metal-free oxidative spirocyclization of hydroxymethylacrylamide with 1,3-dicarbonyl compounds: a new route to spirooxindoles.
A metal-free oxidative spirocyclization of hydroxymethylacrylamide with 1,3-dicarbonyl compounds is described. The reaction proceeds through tandem dual C-H functionalization and intramolecular dehydration, in which two new C-C bonds and one C-O bond were formed. This method affords a novel and straightforward access to various spirooxindoles under mild conditions.
Department of Chemistry, School of Science and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Jiaotong University , Xi'an 710049, China.
Hua
H
Wang
Li-Na
LN
Guo
Xin-Hua
XH
Duan
D000178:Acrylamides / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000178:Acrylamides; D007211:Indoles; D007659:Ketones; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole