2013
DOI: 10.3390/m802
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2'-[(4-Fluorophenyl)carbonyl]-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indole-3,3'-pyrrolizin]-2(1H)-one

Abstract: A new spiro[indole-3,3'-pyrrolizine] derivative is regioselectively synthesized by the straightforward multicomponent reaction of 1-(4-fluorophenyl)-3-phenylprop-2-en-1-one, isatin and L-proline without any catalyst. The structure of the newly synthesized compound is characterized by IR, NMR, UV-visible and mass spectral data. The compound is also screened for its reducing power assay.

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Cited by 4 publications
(4 citation statements)
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“…The structure and regiochemistry of the products were confirmed by spectroscopic analysis. The structure of the newly prepared compounds was proposed by referring to the literature [22,23]. The 1 H NMR spectra of the compounds present only one set of signals and were comparable with that of the literature.…”
Section: Chemistrymentioning
confidence: 70%
“…The structure and regiochemistry of the products were confirmed by spectroscopic analysis. The structure of the newly prepared compounds was proposed by referring to the literature [22,23]. The 1 H NMR spectra of the compounds present only one set of signals and were comparable with that of the literature.…”
Section: Chemistrymentioning
confidence: 70%
“…43 The possible mechanism of this reaction was investigated using a B3LYP/6-311G level of theory, and the results show that the regioselection depends on the energy barrier between the stacking state and the regioisomer. 44 …”
Section: Methodsmentioning
confidence: 99%
“…Benzoheterodiazepine derivatives are designed from different reactants such as cinnamoylacetonitrile [64], hydrazone [65], flavone [66], chalcone [67], α-haloketones [68,69], ethyl acetoacetate [70], cinnamoyl cyanide [71], propargylic alcohols [72], or ketones [73][74][75]. The condensation of diamines (i.e., o-phenylenediamine, o-aminothiophenol, o-aminophenol) and chalcones [76,77] is common under different modes of reactions (i.e., stirring [78], grindstone [79], reflux [80,81], MW [82,83], and ultrasonic irradiations [84,85]) in the presence of catalysts (i.e., piperidine [86,87], NaOH [88,89], NaOAc [90], acetic acid [91,92], trifluoroacetic acid [93], InCl 3 [94], alumina [82], volcanic ash [95], Ti(OiPr) 4 [77], MgO-ZrO 2 [96], SmI 2 [78], SiO 2 [97], Al 2 O 3 [80], TiCl 4 /Sm [98], Bi(NO 3 ) 3 -Al 2 O 3 [99], La Y zeolite [100], HClO 4 -SiO 2 [101], Fe 3 O 4 [102], B(HSO 4 ) 3 …”
Section: Introductionmentioning
confidence: 99%