4-Trifloxy-9-SEM-β-Carboline:  Preparation and Synthetic Utility

Busacca, Carl A.; Eriksson, Magnus; Dong, Yong Qiang; Prokopowicz, Anthony S.; Salvagno, and Annette M.; Tschantz, Matt A.

doi:10.1021/jo990316t

Cited by 22 publications

(13 citation statements)

References 33 publications

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“…We have been interested in evaluating the general utility of our silica gel supported CeCl 3 •7H 2 O/NaI combination by synthesizing methyl 9H-b-carboline-4-carboxylate (10). The method reported in literature requires N-protection, 22 whereas our linear approach involves introduction of the 4-substituent in the first synthetic step (Scheme 3). The product 3ac obtained by the reaction of indole (1a) to the readily available trans-b-nitroacrylate (2c) promoted by CeCl 3 ⋅7H 2 O/NaI/SiO 2 under solvent-free conditions was converted into the tryptamine derivative 8 by hydrogenation in the presence of Raney nickel in ethanol.…”

Section: Methodsmentioning

confidence: 99%

The CeCl₃·7H₂O/NaI/SiO₂ System as an Efficient Promoter for the Friedel-Crafts Reaction of Indoles to Nitroalkenes under Solvent-Free Conditions

Bartoli¹,

Antonio²,

Giuli³

et al. 2008

Synthesis

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The cheap, nontoxic and easy-to-handle CeCl 3 ⋅7H 2 O/NaI Lewis acid promoter is optimal with regard to economic and ecological consideration and allows for useful applications in the synthesis of heterocyclic polyfunctionalized molecules. The procedure becomes efficient if the reaction is carried out under solvent-free conditions and on the surface of CeCl 3 ⋅7H 2 O/NaI supported on silica gel. The simplicity of our method, especially that no precautions need to be taken to exclude moisture or oxygen from the reaction system, permit us to perform the Friedel-Crafts-type conjugate addition of indoles to nitroalkenes. The success of the reaction is independent of the type of indole or nitroalkene used, and provides 3-(2-nitroethyl)indolyl derivatives which are useful building blocks for the synthesis of various types of 3-(2-aminoethyl)indolyl derivatives. These can be subsequently transformed to the b-carbolines with different substituents.

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Section: Methodsmentioning

confidence: 99%

The CeCl₃·7H₂O/NaI/SiO₂ System as an Efficient Promoter for the Friedel-Crafts Reaction of Indoles to Nitroalkenes under Solvent-Free Conditions

Bartoli¹,

Antonio²,

Giuli³

et al. 2008

Synthesis

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“…Busacca described a useful approach for the preparation of 4‐aryl‐, 4‐alkyl‐ and 4‐carboxylate‐substituted β‐carboline derivatives through Pd‐mediated cross‐coupling of arylboronic acids and Grignard reagents. The starting material was the triflate 7 (Scheme ), obtained from THBC by selective oxidation of 6 and aromatization of the pyridine 27…”

Section: Functionalization Of β‐Carboline Systemsmentioning

confidence: 99%

Rh‐Catalyzed [5+1] and [4+1] Cycloaddition Reactions of 1,4‐Enyne Esters with CO: A Shortcut to Functionalized Resorcinols and Cyclopentenones

Fukuyama¹,

Ohta²,

Brancour³

et al. 2012

Chemistry A European J

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We have developed novel Rh-catalyzed [n+1]-type cycloadditions of 1,4-enyne esters, which involve an acyloxy migration as a key step. The efficient preparation of functionalized resorcinols, including biaryl derivatives, from readily available 1,4-enyne esters and CO was achieved by Rh-catalyzed [5+1] cycloaddition accompanied by 1,2-acyloxy migration. When enyne esters had an internal alkyne moiety, the reaction proceeded by a [4+1]-type cycloaddition involving 1,3-acyloxy migration, leading to cyclopentenones.

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“…The starting material was the triflate 7 (Scheme 15), obtained from THBC by selective oxidation of 6 and aromatization of the pyridine. [27] Scheme 15.…”

Section: Asymmetric Alkylations Of Thbcs At the 1-and The 4-positionsmentioning

confidence: 99%

Chemistry of β‐Carbolines as Synthetic Intermediates

Domı́nguez

Pérez‐Castells

2011

Eur J Org Chem

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Abstractβ‐Carbolines are present in a wide variety of indole alkaloids that display important biological activities. Here we review the most recent aspects of the chemistry of β‐carbolines with a focus on functionalization of the β‐carboline system and transformations into other interesting compounds. Aromatizations, reductions and alkylations of the heterocyclic system are thus summarized first, followed by methodologies directed towards the formation of additional fused rings. Finally, rearrangements that transform β‐carbolines into other heterocyclic systems are covered.

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4-Trifloxy-9-SEM-β-Carboline: Preparation and Synthetic Utility

Cited by 22 publications

References 33 publications

The CeCl₃·7H₂O/NaI/SiO₂ System as an Efficient Promoter for the Friedel-Crafts Reaction of Indoles to Nitroalkenes under Solvent-Free Conditions

The CeCl₃·7H₂O/NaI/SiO₂ System as an Efficient Promoter for the Friedel-Crafts Reaction of Indoles to Nitroalkenes under Solvent-Free Conditions

Rh‐Catalyzed [5+1] and [4+1] Cycloaddition Reactions of 1,4‐Enyne Esters with CO: A Shortcut to Functionalized Resorcinols and Cyclopentenones

Chemistry of β‐Carbolines as Synthetic Intermediates

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4-Trifloxy-9-SEM-β-Carboline: Preparation and Synthetic Utility

Cited by 22 publications

References 33 publications

The CeCl3·7H2O/NaI/SiO2 System as an Efficient Promoter for the Friedel-Crafts Reaction of Indoles to Nitroalkenes under Solvent-Free Conditions

The CeCl3·7H2O/NaI/SiO2 System as an Efficient Promoter for the Friedel-Crafts Reaction of Indoles to Nitroalkenes under Solvent-Free Conditions

Rh‐Catalyzed [5+1] and [4+1] Cycloaddition Reactions of 1,4‐Enyne Esters with CO: A Shortcut to Functionalized Resorcinols and Cyclopentenones

Chemistry of β‐Carbolines as Synthetic Intermediates

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The CeCl₃·7H₂O/NaI/SiO₂ System as an Efficient Promoter for the Friedel-Crafts Reaction of Indoles to Nitroalkenes under Solvent-Free Conditions

The CeCl₃·7H₂O/NaI/SiO₂ System as an Efficient Promoter for the Friedel-Crafts Reaction of Indoles to Nitroalkenes under Solvent-Free Conditions