N-Alkylation of 1H-indoles and 9H-carbazoles with alcohols

Bombrun, Agnès; Casi, Giulio

doi:10.1016/s0040-4039(02)00217-4

Cited by 37 publications

(21 citation statements)

References 5 publications

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“…[4e,41,42,59,60] With the use of cyanomethylenetrimethylphosphorane 12 (R ϭ Me) primary and secondary alcohols can be transformed into nitriles with acetone cyanohydrin, [41] primary alcohols can be converted into amines [61] or into one-carbon-atom extended nitriles, [62] and primary, secondary, and tertiary alcohols can be used for alkylation of 1H-indole and 9H-carbazole derivatives. [63] The phosphorane reagents are generally less active at room temperature.…”

Section: Alternative Reagentsmentioning

confidence: 99%

Recent Advances in the Mitsunobu Reaction: Modified Reagents and the Quest for Chromatography‐Free Separation

Dembiński

2004

Eur J Org Chem

179

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Section: Alternative Reagentsmentioning

confidence: 99%

Recent Advances in the Mitsunobu Reaction: Modified Reagents and the Quest for Chromatography‐Free Separation

Dembiński

2004

Eur J Org Chem

179

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“…Primary and secondary alcohols are mainly used as alkylating agents in the Mitsunobu reaction, although there are examples of the use of tertiary alcohols [20]. The Mitsunobu reaction is widely used for the construction of cyclic structures [3,6].…”

Section: The General Characteristics and Certain Aspects Of The Mechamentioning

confidence: 99%

The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)

Голанцов

Карчава

Yurovskaya

2008

Chem Heterocycl Comp

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Methods for the design of nitrogen-containing heterocyclic systems involving the formation of C-N bonds under the conditions of the Mitsunobu reaction are discussed.The Mitsunobu reaction [1][2][3][4] is the reaction of compounds containing a mobile hydrogen atom HX with alcohols in the presence of a reagent system consisting of an azodicarboxylic ester and a phosphine PR 1 3 . This reaction results in the formation of an alkylation product RX accompanied by oxidation of the phosphine PR 1 3 to phosphine oxide R 1 3 P=O and reduction of the azodicarboxylic ester to the corresponding hydrazine.The reaction takes place under very mild conditions and usually at room temperature. If a chiral secondary alcohol ROH is used, the reaction is usually stereospecific and is accompanied by inversion of the configuration at the asymmetric carbon atom of the alcohol [1-3].From the moment of the first report [5] the Mitsunobu reaction became a powerful tool in synthetic organic chemistry and found widespread use in the synthesis of various heterocyclic compounds, optically active substances, steroids, alkaloids, carbohydrates, and nucleosides [1][2][3][4]6]. In particular, in a number of cases the Mitsunobu reaction has made it possible to synthesize new physiologically active compounds or to put forward new highly effective approaches to synthesis. Several reviews have been devoted to the Mitsunobu reaction [1-4, 6, 7]. Data on the use of the Mitsunobu reaction in the synthesis of alkaloids were reviewed in [6]. Various experimental techniques that make it possible to simplify the isolation of the products of the Mitsunobu reaction RX from the reaction mixture, including the use of reagents attached to a polymer support, were discussed in [7]. _______ * Dedicated to Afanasi Andreevich Akhrem on his 95th birthday. _________________________________________________________________________________________

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“…Carbazole derivatives having nitrogen containing rigid aromatic heterocyclic moiety with desirable electronic charge transfer properties along with an extended π -conjugated system [8] exhibit diverse biological activities such as antibacterial [3, 9, 10], antifungal [11, 12], antiviral [13], anticancer [14], and various other activities. Besides the general antibacterial activity, carbazoles were shown to have a significant antituberculosis activity [15, 16].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity of Murrayaquinone A and 6-Methoxy-3,7-dimethyl-2,3-dihydro-1H-carbazole-1,4(9H)-dione

Chakraborty

Saha

2014

International Journal of Microbiology

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The antibacterial activity of Murrayaquinone A (10), a naturally occurring carbazoloquinone alkaloid, and 6-methoxy-3,7-dimethyl-2,3-dihydro-1H-carbazole-1,4(9H)-dione (11), a synthetic carbazoloquinone, both obtained during the development of the synthesis of Carbazomycin G, having unique quinone moiety, was studied against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas sp.) bacteria. Compound 10 showed antibacterial activities against both of Escherichia coli and Staphylococcus aureus whereas compound 11 indicated the activity against Staphylococcus aureus only. Both compounds 10 and 11 exhibited minimum inhibitory concentration (MIC) of 50 μg mL−1 against Staphylococcus aureus.

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N-Alkylation of 1H-indoles and 9H-carbazoles with alcohols

Cited by 37 publications

References 5 publications

Recent Advances in the Mitsunobu Reaction: Modified Reagents and the Quest for Chromatography‐Free Separation

Recent Advances in the Mitsunobu Reaction: Modified Reagents and the Quest for Chromatography‐Free Separation

The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)

Antibacterial Activity of Murrayaquinone A and 6-Methoxy-3,7-dimethyl-2,3-dihydro-1H-carbazole-1,4(9H)-dione

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