The Michael Addition of Indoles to α,β-Unsaturated Ketones Catalyzed by CeCl3·7H2O−NaI Combination Supported on Silica Gel1

Bartoli, Giuseppe; Bartolacci, Massimo; Bosco, Marcella; Foglia, Gioia; Giuliani, Arianna; Marcantoni, Enrico; Sambri, Letizia; Torregiani, Elisabetta

doi:10.1021/jo034303y

Cited by 156 publications

(49 citation statements)

References 42 publications

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“…All obtained products, except 5c, are known compounds and were identified by comparison of 1 H and 13 C NMR spectra with literature data. Spectroscopic data of 5c are given below.…”

Section: Experimental Section Typical Experimental Procedures For Allymentioning

confidence: 99%

“…[10] In conclusion, the synthesis of a (Z)-allyl alcohol is still an unsolved problem. [11] During our program to develop new synthetic uses of the CeCl 3 · 7 H 2 O/NaI [12] combination in promoting C À C bond formation, [13] we found that this system strongly facilitates the addition of allyltributylstannane to aldehydes in CH 3 CN. [14] We report now that by this protocol a highly regio-and stereoselective addition of the 2-alkenyltributyltin derivative is accomplished surprisingly leading to the prevalent formation of the a-adduct in the less stable (Z)-configuration.…”

Section: Introductionmentioning

confidence: 99%

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Allylation of Aldehydes Promoted by the Cerium(III) Chloride Heptahydrate/Sodium Iodide System: the Dependence of Regio‐ and Stereocontrol on the Reaction Conditions

Bartoli¹,

Giuliani²,

Marcantoni³

et al. 2005

Adv Synth Catal

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Abstract:The cerium(III) chloride heptahydrate/sodium iodide complex (CeCl 3 · 7 H 2 O/NaI) acts as a useful promoter in the carbon-carbon bond forming reaction by addition of allyltributylstannanes to aldehydes. The reaction of 2-butenyltributylstannane shows that the regio-and the stereochemical outcomes depend on the reaction conditions. When the promoter is adsorbed on a solid support (aluminum oxide), a highly prevalent formation of the g-adduct is observed in solvent-free conditions. Conversely, when the reaction is carried out in acetonitrile as the solvent, the a-adduct largely prevails. In the last case, a complete stereocontrol is observed, the less stable (Z)-isomer being obtained in high geometrical purity.

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“…All obtained products, except 5c, are known compounds and were identified by comparison of 1 H and 13 C NMR spectra with literature data. Spectroscopic data of 5c are given below.…”

Section: Experimental Section Typical Experimental Procedures For Allymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Allylation of Aldehydes Promoted by the Cerium(III) Chloride Heptahydrate/Sodium Iodide System: the Dependence of Regio‐ and Stereocontrol on the Reaction Conditions

Bartoli¹,

Giuliani²,

Marcantoni³

et al. 2005

Adv Synth Catal

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“…Substituted indoles are capable of binding to many receptors with high affinity. Therefore, the synthesis and selective functionalization of indoles have been the focus of active research over the years [11][12][13][14][15][16][17]. Promoted from the above findings and as a continuation of our research interest in synthesis and biological activities of novel derivatives of some heterocyclic compounds [18][19][20], the present study aimed to synthesis and to evaluate antioxidant potentials of novel indole-2-carboxylic acid analogues.…”

Section: Introductionmentioning

confidence: 99%

Novel indole-2-carboxylic acid analogues: Synthesis and a new light in to their antioxidant potentials

2012

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KEYWORDSTwo series of novel indole-2-carboxylic acid derivatives is reported. In the first series, Nsubstituted derivatives (3a-h) were synthesized via acylation of indole-2-carboxylic acid followed by aldol condensation reaction. Whereas, in the second series, indole-2-carboxamides (5a-g) were synthesized through conversion of acid to its acid chloride followed by coupling of substituted anilines. Structures of the newly synthesized compounds were confirmed by elemental analysis and spectral IR, 1 H NMR and mass data and were screened for antioxidant activity. Among the first series, compound 3g showed higher antioxidant activity and whereas, in the second series compounds 5b and 5c exhibited potential antioxidant activity. Compounds 3g, 5b and 5c exhibited for its enhanced antioxidant activity.

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“…[1][2][3] The results suggest that the total synthetic process in aqueous systems is simple and the interface between the solid phase and the aqueous liquid provides specificity and diversity in the synthetic reactions. On the other hand, many attempts at chromatographic determination of analytes coupled with the derivatization reaction have been made to overcome the problems of low detection and insufficient separation.…”

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confidence: 97%

Tosylation of Endocrine-Disruptive Alkylphenolic Compounds in a Solid-Phase Reaction System Consisting of C18-Modified Silica Gel and Aqueous Buffer Solution

Uno

Okumura

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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Recently, much attention has been paid to synthetic organic reactions in aqueous media instead of in organic solvents such as silica gel-dispersal and polymer-dispersal aqueous systems from the point of view of environmental conservation. [1][2][3] The results suggest that the total synthetic process in aqueous systems is simple and the interface between the solid phase and the aqueous liquid provides specificity and diversity in the synthetic reactions. On the other hand, many attempts at chromatographic determination of analytes coupled with the derivatization reaction have been made to overcome the problems of low detection and insufficient separation. 4) However, the derivatization techniques utilizing the solid phase and solid phase-dispersed reactions have only been discussed in terms of efficiency in the analytical procedure, that is, efficient conversion of the analytes to the derivatives, high recovery, and shortening of the analysis time. [5][6][7][8][9] In particular, trace analyses of biological samples have been developed coupled with on-column derivatization and micro solid-phase extraction techniques. 6,7) However, environmental analyses still essentially require an enrichment step such as preconcentration and a derivatization step to achieve low detection limits prior to chromatographic separation. 10) The solid-phase aqueous reaction is a desirable method for environmental analyses from the point of view of environmental conservation as well as efficiency in the analytical procedure.The derivatization reagents characterized by an active sulfonyl chloride to the phenolic hydroxyl group such as tosyl chloride (4-methylbenzenesulfonyl chloride), dansyl chloride, and ferrocenesulfonyl chloride are entirely used for precolumn derivatization to overcome the disadvantage of the background response. Precolumn dansylation is applied to the HPLC analysis of endocrine-disruptive alkylphenolic compounds in environmental water. 10) The solid-phase reaction of the sulfonyl chlorides is important in improving the analytical methods. In this study, we have developed a direct tosylation method for alkylphenolic compounds preconcentrated in a C 18 -modified silica gel (ODS) cartridge used for their enrichment step using a heterogeneous system consisting of an aqueous medium and ODS instead of organic solvents, as a prototype of the solid-phase derivatization method of the phenols with sulfonyl chlorides. ExperimentalChemicals Tosyl chloride as a derivatization reagent was purchased from Nacalai Tesque and used as received without further purification. The samples used were alkylphenols [4-tert-butylphenol, 4-sec-butylphenol, 4-(1,1-dimethylpropyl)phenol, 4-(1,1,3,3-tetramethylbutyl)phenol, and 4-nonylphenol] which are recognized as estrogenic compounds. 10) They were of the best available grade from Nacalai Tesque and Tokyo Chemical Industry and were used as received. The ODS powder was purchased from Nacalai Tesque and was used in the solid-phase disperse system as a solidphase catalyst.Preparation of the Standa...

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The Michael Addition of Indoles to α,β-Unsaturated Ketones Catalyzed by CeCl₃·7H₂O−NaI Combination Supported on Silica Gel¹

Cited by 156 publications

References 42 publications

Allylation of Aldehydes Promoted by the Cerium(III) Chloride Heptahydrate/Sodium Iodide System: the Dependence of Regio‐ and Stereocontrol on the Reaction Conditions

Allylation of Aldehydes Promoted by the Cerium(III) Chloride Heptahydrate/Sodium Iodide System: the Dependence of Regio‐ and Stereocontrol on the Reaction Conditions

Novel indole-2-carboxylic acid analogues: Synthesis and a new light in to their antioxidant potentials

Tosylation of Endocrine-Disruptive Alkylphenolic Compounds in a Solid-Phase Reaction System Consisting of C18-Modified Silica Gel and Aqueous Buffer Solution

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