PTSA‐Catalyzed Reaction of Indoles with 2‐Oxoaldehydes: Synthesis of α,α‐Bis(indol‐3‐yl) Ketones

Suárez, Anisley; Martı́nez, Fernando; Suárez‐Pantiga, Samuel; Sanz, Roberto

doi:10.1002/slct.201700013

Cited by 13 publications

(10 citation statements)

References 37 publications

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“…In 2020, Sanz et al presented an approach combining gold and molybdenum catalysis . On the basis of previous works on similar substrates, , the nitro-functionalized alkynol 134 bearing two indole substituents was successfully converted into indolocarbazole 135 (Scheme ). In the first step, 5 mol % of NaAuCl 4 was used.…”

Section: Extended Anellated Aromatic Systemsmentioning

confidence: 99%

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

et al. 2020

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Often stoichiometric amounts of gold find use in materials science; occasionally gold is even used as a support. This review discusses the contributions of gold catalysis, both homogeneous and heterogeneous, to the field of materials science. One topic is the synthesis of polymers, including nanowires and polyesters, the postcyclization of polymers, polymerization by cyclopropanation, and gold-catalyzed radical polymerization reactions. Other topics are dyes, phosphonium salts, and a wide range of extended conjugated π-systems, the latter ranging from acenes, pentalene derivatives, and different heterocyclic π-systems to fascinating applications in the synthesis of helical anellated aromatic molecules. The existing contributions clearly demonstrate the potential of gold catalysis for significant future impulses for the field of materials science.

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Section: Extended Anellated Aromatic Systemsmentioning

confidence: 99%

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

et al. 2020

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“…To start our investigations, we selected 3,3-bis(indolyl)methane derivative 1a as model substrate. For its preparation we took advantage of our previously reported efficient synthesis of α,α-bis(indol-3-yl) ketones from commercially available indoles and 2-oxoaldehydes under Brønsted acid catalysis . Their reactions with lithium or magnesium acetylides afford the corresponding alkynols 1 used in this work .…”

mentioning

confidence: 99%

Gold-Catalyzed Synthesis of 1-(Indol-3-yl)carbazoles: Selective 1,2-Alkyl vs 1,2-Vinyl Migration

et al. 2017

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Gold(III)-catalyzed cycloisomerization of α-bis(indol-3-yl)methyl alkynols selectively affords 1-(indol-3-yl)carbazoles, in a transformation that takes place through a selective 1,2-alkyl vs 1,2-vinyl migration step in the vinyl-gold intermediate generated from the initial 5-endo-spirocyclization. The reaction proceeds well with either tertiary or secondary starting alkynols as well as with a wide variety of alkyne substituents. The key role of the other indol-3-yl substituent for the unexpected selectivity in the 1,2 rearrangement has also been supported by DFT calculations that reveal a low barrier, two-step mechanism in the alkyl migration path where the second indole significantly stabilizes a carbocationic intermediate.

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“…Arylglyoxals are widely used in syntheses of heterocycles as syntones. [1][2][3][4][5][6] But the study of the arylglyoxals interaction with N-hydroxyurea [7][8][9] and its derivatives 8,10 has started recently and needs to be continued.…”

Section: Introductionmentioning

confidence: 99%

3-Alkoxy-1,5-Diaryl-4,5-Dihydroxyimidazolidin-2-Ones and 3-Alkoxy-1-Alkyl-5-Aryl-4,5-Dihydroxyimidazolidin-2-Ones: Synthesis and Structure

Штамбург

Shtamburg

Anishchenko³

et al. 2019

ECB

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It has been found that 4-nitrophenylglyoxal reacts with N-alkoxy-N'-arylureas and N-alkoxy-N'-alkylureas in acetic acid medium with the selective formation of the diastereomers of the 3-alkoxy-1,5-diaryl-4,5-dihydroxyimidazolidin-2-ones and 3-alkoxy-1-alkyl-5-aryl-4,5dihydroxyimidazolidin-2-ones with cis-orientation of OH-groups. The X-ray structural analysis of 3-propyloxy-4S,5S-4,5-dihydroxy-1methyl-5-(4-nitrophenyl)imidazolidin-2-one and of 3-n-butyloxy-4S,5S-4,5-dihydroxy-1-(4-methylphenyl)-5-(4-nitrophenyl)imidazolidin-2-one has demonstrated this structural feature of these compounds.

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PTSA‐Catalyzed Reaction of Indoles with 2‐Oxoaldehydes: Synthesis of α,α‐Bis(indol‐3‐yl) Ketones

Cited by 13 publications

References 37 publications

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

Gold-Catalyzed Synthesis of 1-(Indol-3-yl)carbazoles: Selective 1,2-Alkyl vs 1,2-Vinyl Migration

3-Alkoxy-1,5-Diaryl-4,5-Dihydroxyimidazolidin-2-Ones and 3-Alkoxy-1-Alkyl-5-Aryl-4,5-Dihydroxyimidazolidin-2-Ones: Synthesis and Structure

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