2005
DOI: 10.1021/jo048776w
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Efficient Preparation of 2-Indolyl-1-nitroalkane Derivatives Employing Nitroalkenes as Versatile Michael Acceptors:  New Practical Linear Approach to Alkyl 9H-β-Carboline-4-carboxylate

Abstract: The combination of cerium(III) chloride heptahydrate and sodium iodide supported on silica gel is known to promote Michael-type additions. Continuing our work on solvent-free conditions, the CeCl3.7H2O-NaI-SiO2 system catalyzes the addition of a variety of indoles and nitroalkenes, giving 2-indolyl-1-nitroalkane derivatives in good yields. Development of this method has resulted in a new protocol for the synthesis of 4-substituted beta-carbolines.

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Cited by 98 publications
(35 citation statements)
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“…The addition of electron rich aromatics such as indole derivatives to 1 is known to be promoted by CeCl 3 /NaI supported on silica. 33 There also exists an organocatalysed asymmetric protocol. 34 Synthesis of the indole addition product 3 was straightforward (91%) and the literature conditions could also be used with trimethoxybenzene to give 4 in 87% yield (Equation 1).…”
Section: Resultsmentioning
confidence: 99%
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“…The addition of electron rich aromatics such as indole derivatives to 1 is known to be promoted by CeCl 3 /NaI supported on silica. 33 There also exists an organocatalysed asymmetric protocol. 34 Synthesis of the indole addition product 3 was straightforward (91%) and the literature conditions could also be used with trimethoxybenzene to give 4 in 87% yield (Equation 1).…”
Section: Resultsmentioning
confidence: 99%
“…In an identical procedure as to the preparation of 6, nitroacrylate 1 (100 mg, 0.69 mmol) in EtOH (7 mL) after purification by flash column chromatography (Petrol:Et 2 O 9:1) gave nitroalkane 7 (117 mg, 89%) as a colourless oil; R f 0. 33 …”
Section: Ethyl 2-ethoxy-3-nitropropanoate (7)mentioning
confidence: 99%
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“…We then decided to evaluate some of the experimental results available in the literature on the Michael-type addition of various carbon-and heteroatom-centered nucleophiles to conjugated nitroalkenes. The representative examples chosen from the literature involve reactions of nitroalkenes with heteroatom nucleophiles (2-aminobenzaldehyde), [39] Ccentered nucleophiles (indole and malonate), [40,41] and an organometallic reagent (Fischer aminocarbene complex). [42] Our analysis has shown that the parameters discussed above [local softness (s + β-C ), the β-CED and Fukui function (f + β-C )] correlate well with the isolated yields in a majority of the cases and moderately well with the reaction time (see Supporting Information for further discussion).…”
Section: Substituent Effect On the Reactivity Of Nitroalkenes As Michmentioning
confidence: 99%
“…The nitroolefins are recognized as excellent Michael aceptors 48,49 and their derivatives are important intermediates in organic synthesis due to the synthetic versatility of the nitro-group as precursor of other organic functionalities. [50][51][52] First, we investigated the reaction of indole 1a wiyh nitrostyrene 4a carried out under the reactions conditions described above (i-PrOH, room temperature and 10 mol% of SnCl 2 ·2H 2 O).…”
Section: Reactions Of Indoles With Nitrostyrenesmentioning
confidence: 99%