2015
DOI: 10.1002/jhet.2542
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Novel Tetraindoles and Unexpected Cycloalkane Indoles from the Reaction of Indoles and Aliphatic Dialdehydes

Abstract: The reaction of indoles with dialdehydes was studied for the first time. Mild reaction conditions using glacial acetic acid led to two novel kinds of reaction products: one designated as alkyl chain‐connected tetraindoles and the other one as bis(indolyl)‐substituted cycloalkane indoles. The suggested reaction pathways are discussed. The indole substituents of the cycloalkane indoles were either trans or cis orientated depending from the alkyl chain length.

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Cited by 2 publications
(2 citation statements)
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References 18 publications
(19 reference statements)
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“…The product formation proceeded via the dicarbinol intermediate A resulting from an aldehyde function attack to each electron-rich C-3 position of one indole similar to the recently reported reaction of aliphatic dialdehydes with indole 31. The following cyclization reaction to intermediates B and C resulted from a second attack of the respective alcoholic function of the origin aldehyde to the neighbored C-2 of the respective indole.…”
Section: Resultssupporting
confidence: 55%
“…The product formation proceeded via the dicarbinol intermediate A resulting from an aldehyde function attack to each electron-rich C-3 position of one indole similar to the recently reported reaction of aliphatic dialdehydes with indole 31. The following cyclization reaction to intermediates B and C resulted from a second attack of the respective alcoholic function of the origin aldehyde to the neighbored C-2 of the respective indole.…”
Section: Resultssupporting
confidence: 55%
“…More contexts on cycloalkanes and its applications can refer to El-Sayed et al [30], Vásquez-Espinal et al [31], Caroen et al [32], Denicourt-Nowicki et al [33], El-Gamal et al [34,35], Lepori et al [36], Nambu et al [37], Lazić et al [38], Alaoui et al [39], and Pi-Boleda et al [40]. Since cycloalkanes commonly appeared in the chemical compound and possess wide engineering applications in the field of biology, medicine, and pharmacy, it inspires us to study the characterization of cycloalkanes from mathematical point of view.…”
Section: Introductionmentioning
confidence: 99%