An efficient stereoselective synthesis of 3-spirocyclopentene- and 3-spiropyrazole-2-oxindoles via 1,3-dipolar cycloaddition reaction.
The chemistry phosphorus and sulfur ylides have been exploited for a facile, short and efficient synthesis of 3-spirocyclopentene- and 3-spiropyrazole-2-oxindoles from E- and Z-isomers of bromo derivatives of Morita-Baylis-Hillman adducts of isatin with Ph(3)P/activated alkene/K(2)CO(3) and Me(2)S/DEAD/K(2)CO(3), respectively, via [3 + 2]-annulation strategy.
Selvakumar
Kodirajan
K
Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology, Trivandrum-695 019, Kerala, India.
Vaithiyanathan
Vadivel
V
Shanmugam
Ponnusamy
P
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D000078183:Oxindoles; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000475:Alkenes; D007211:Indoles; D000078183:Oxindoles; D011720:Pyrazoles; D013141:Spiro Compounds; C022960:2-oxindole