CAN and iodine-catalyzed reaction of indole or 1-methylindole with α,β-unsaturated ketone or aldehyde

Ko, Shengkai; Lin, Chun‐Chi; Tu, Zhijay; Wang, Yi‐Fu; Wang, Chieh Chieh; Yao, Ching Fa

doi:10.1016/j.tetlet.2005.11.058

Cited by 67 publications

(31 citation statements)

References 52 publications

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“…In fact, bi‐, tri‐, and multiple alkylation processes generally occur simultaneously, thereby leading to useless chemical outcomes for synthetic applications (Figure 7). 40 The absence of metal‐promoted chemoselective Michael additions of indoles to enals in the literature illustrates the intrinsic difficulties of such a transformation.…”

Section: Reactions With Cc Multiple Bondsmentioning

confidence: 99%

Catalytic Functionalization of Indoles in a New Dimension

2009

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140 years ago Adolf von Baeyer proposed the structure of a heteroaromatic compound which revolutionized organic and medical chemistry: indole. After more than a century, indole itself and the complexity of naturally occurring indole derivatives continue to inspire and influence developments in synthetic chemistry. In particular, the ubiquitous presence of indole rings in pharmaceuticals, agrochemicals, and functional materials are testament to the ever increasing interest in the design of mild and efficient synthetic routes to functionalized indole derivatives. This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.

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Section: Reactions With Cc Multiple Bondsmentioning

confidence: 99%

Catalytic Functionalization of Indoles in a New Dimension

2009

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“…There are many reactions known for the synthesis of oxindole derivatives by condensation of isatins and indoles in the presence of various catalysts [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]. Although these methods work well, many of them involve harsh reaction conditions, long reaction time, or the use of corrosive acids.…”

Section: Introductionmentioning

confidence: 99%

Tungstic acid-catalyzed synthesis of 3,3-bis (1H-indol-3-yl)indolin-2-one derivatives

Patel

Deota

2013

Heterocyclic Communications

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Tungstic acid was used as a low-cost and readily available heterogeneous catalyst for the synthesis of 3,3-bis(1H-indol-3-yl)indolin-2-one derivatives from indoles. The reaction parameters, including catalyst quantity, solvents, temperature, and time were optimized. The present method has several advantages, such as mild conditions, simple work-up, elimination of anhydrous condition, easy recovery of catalyst and its recyclability as compared with existing methods.

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“…solvent for this transformation (entries [7][8][9]. It turned out that for substrate (2a) the loading significantly affected the yield, with a 71% yield obtained using 2 equiv.…”

mentioning

confidence: 99%

“…Initially, a variety of aldehydes were reacted with 2-(phenylethynyl)aniline (1a) (entries [1][2][3][4][5][6][7][8][9]. The results showed that both electrondonating and electron-withdrawing groups, such as methyl, methoxy, chloro, bromo and nitro, were well tolerated on the aromatic ring of the aldehydes (entries 1-8).…”

mentioning

confidence: 99%

Silver Nitrate Catalysed Tandem Reactions of O-Ethynylanilines with Aryl Aldehydes: Selective One-Pot Synthesis of Bis(Indolyl)Methanes

Tang

2012

Journal of Chemical Research

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Bis(indolyl)methanes are an important class of indole derivatives that have been widely used in medical treatments. A novel silver nitrate-catalysed one-pot synthesis of bis(indolyl)methanes has been developed. In the presence of silver nitrate, cycloisomerisation and bis-addition of o-ethynylanilines with aromatic aldehydes were carried out efficiently to afford the corresponding bis(indolyl)methanes in good to excellent yields.

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CAN and iodine-catalyzed reaction of indole or 1-methylindole with α,β-unsaturated ketone or aldehyde

Cited by 67 publications

References 52 publications

Catalytic Functionalization of Indoles in a New Dimension

Catalytic Functionalization of Indoles in a New Dimension

Tungstic acid-catalyzed synthesis of 3,3-bis (1H-indol-3-yl)indolin-2-one derivatives

Silver Nitrate Catalysed Tandem Reactions of O-Ethynylanilines with Aryl Aldehydes: Selective One-Pot Synthesis of Bis(Indolyl)Methanes

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