- Alkylation of the ambident indole ion in ionic liquids
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Alkylation of the ambident indole anion in ionic liquids has been investigated. The reaction rate is greater in ionic liquids than in organic solvents. The polarity of certain ionic liquids has been determined to be located between methanol and acetonitrile. 2008 Springer Science+Business Media, Inc.
- Vavilina,Zicmanis,Drozdova,Mekss,Klavins
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p. 530 - 541
(2013/07/27)
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- A convenient one step anodic synthesis of 3-alkyl indoles
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3-Alkyl indoles have been synthesized anodically by co-electrolysis of indole-3-propanoic acid 1 and mono carboxylic acids 2a-2f viz. propanoic acid 2a, hexanoic acid 2b, nonanoic acid 2c, decanoic acid 2d, dodecanoic acid 2e and hexadecanoic acid 2f at platinum, titanium and graphite. The dimeric products obtained are viz. 1,4 (3′-diindolyl) butane 1′, alkanes 2′a-2′f and 3-alkyl indoles 3′a-3′f. These products have been separated by column chromatography using different solvents and characterized by IR, 1H NMR and elemental analysis. These studies have suggested that the desired product 3′a-3′f is obtained in 33-60% yield at platinum anode at current density 0.1111 A.cm-2.
- Yadav, Ashok K.,Singh, Arpita,Prakash, Lalit
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p. 1274 - 1278
(2007/10/03)
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- Regioselectivity Control in Alkylation Reactions of Indolyl Ambident Anion
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The regioselectivity of N- and C-3(β)-alkylations of indolylmetal salts was studied under various conditions.The effect of counter metal ion is crucial in determining the regioselectivity.In tetrahydrofuran, exclusive N-alkylation occurred with the potassium salt, but the extent of C-3-alkylation increased with the sodium and lithium salts and became predominant with the magnesium bromide salt.However, N-alkylation was favoured generally in more polar solvents and for alkyl toluene-p-sulphonates it was favoured even with magnesium bromide salts.The reactivity and regioselectivity of the alkylations were correlated with the calculated electron density of the indolyl anion and with 13C n.m.r. chemical shifts of the metal salts.
- Nunomoto, Sadaaki,Kawakami, Yuhsuke,Yamashita, Yuya,Takeuchi, Hisato,Eguchi, Shoji
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p. 111 - 114
(2007/10/02)
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- A NEW CARBON-CARBON BOND FORMING REACTION IN INDOLE CHEMISTRY. C3-ARYLATION AND ALKYLATION WITH PHENYL (β-INDOLYL)IODONIUM TRIFLUOROACETATE
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Phenyl(β-indolyl)iodonium trifuoroacetate was reacted with various alkyl and aryllithiums (CH3, n-C4H9, C3H5, C6H5) in BF3Et2O/THF to yield C3-alkylation and arylation of the indole nucleus with reductive elimination of iodobenzene.
- Moriarty, Robert M.,Ku, Y. Y.,Sultana, M.,Tuncay, Atilla
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p. 3071 - 3074
(2007/10/02)
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