Crystal structure of 2-spiro-3′-(2-oxindole)-3-benzoyl-4-phenyl-5- hydroxymethylpyrrolidine, C25H22N2O3

Abstract

C 25 H 22 N 2 O 3 ,monoclinic, P2 1 /n (no. 14), a =14.323(1) Å, Source of materialAmixture of the isatin (0.147 g, 1mmol), L-serine (0.105 g, 1 mmol) and chalcone (0.250 g, 1.2 mmol) in methanol (20 mL) was stirred under reflux for 4hours. After completion of the reaction, it was evaporated to dryness, followed by chromatography to the pure title compound (yield, 0.305 g, 84.2 %).

Crystal structure of spiro[(indane-1,3-dione)-2,3'-(2'-methyl-2'- methyloxycarbonyl-hexahydro-1'H-pyrrolizine)], C18H19NO4

“…In this reaction,t he azomethine ylidei sf irstly generated in situ,v ia decarboxylative condensation of an aldehyde or aketone with an amino acid, which is trapped smoothly by trapping dipolarophiles to form five-membered heterocyclic compounds [2,3].Almost all these reactions run with ag ood yield and high regio-and stereoselectivity [1][2][3][4]. The two components of the title crystal structure, indane-1,3-dione and hexahydro-pyrrolizine,j oin at the spiroquaternary carbon (C1).…”

Spiro indane-1,3-dione pyrrolizidine compounds synthesized by 1,3-dipolar cyclo-addition reaction

“…The 1,3-dipolar cyclo-addition reaction provides a simple and direct entry into a number of fi ve-membered heterocyclic compounds, such as pyrrolidines, pyrrolines and pyrroles (Okino et al , 2005 ;Chen et al , 2009 ;Miao et al , 2010 ). In this reaction, the azomethine ylides are generated in situ via decarboxylative condensation of aldehyde or ketone with α -amino acids.…”

“…The ylides can be trapped by dipolarophiles to form fi ve-membered heterocyclic compounds (Huisgen , 1968 ). Almost all these reactions proceed with good yield and with high regio-and stereoselectivity (Huisgen , 1968 ;Okino et al , 2005 ;Chen et al , 2009 ;Miao et al , 2010 ). Until now, very little attention has been paid to regioselectivity of this reaction.…”