An improved preparation of isatins from indoles

Tatsugi, Jiro; Tong, Zhiwei; Izawa, Yasuji

doi:10.3998/ark.5550190.0002.105

Cited by 19 publications

(13 citation statements)

References 9 publications

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“…The reaction is thought to proceed via a 3,3dibromooxindole as an intermediate. 1523 The reaction was carried out with a mixture of 1-alkyl-7-azaindole, NBS, and anhydrous DMSO at 60 °C for 6 h, and then the reaction was Fuchs and Funk have isolated and used 3-alkyl-3bromooxindole as a key intermediate in the elegant syntheses of (±)-flustramines A and C. 1524 In this case, 3-alkyl-6bromoindole was treated with NBS in a mixture of tert-butyl alcohol, THF, and water to afford the key 3-alkyl-3-bromo-6bromoindolin-2-one (Scheme 552). Tian et al developed a procedure for the conversion of a 1methyl-1H-indole derivative to the corresponding 1-methylindolin-2-one derivative via an NBS-assisted oxidative transformation.…”

Section: Application Of Nbs To Oxidation Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Application Of Nbs To Oxidation Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…Detailed Investigation on Reversible Hydration-Dehydration of DPPT Before the development of a new polymer bearing vicinal tricarbonyl moiety and the investigation on its reversible hydration-dehydration behaviors, DPPT was synthesized according to the literature (Scheme 2) 23 to investigate its hydration behavior as a model for the polymer system: 1,3-Dipheny-1,3-propnanedione was oxidized with NBS in DMSO followed by sublimation at 80 C under reduced pressure (0.45 mmHg). As a result, DPPT was obtained as a yellow powder in 95% yield.…”

Section: Resultsmentioning

confidence: 99%

Construction of reversible hydration–dehydration system by a model compound and a novel polymer bearing vicinal tricarbonyl structure

Dei

Morino

Sudo

et al. 2011

J. Polym. Sci. A Polym. Chem.

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A novel polymer bearing acyclic vicinal tricarbonyl moieties in the side chains was synthesized by (1) radical polymerization of a styrene derivative with a 1,3-diketone structure and (2) successive treatment of the resulting polystyrene derivative by N-bromosuccinimide to convert its 1,3-diketone moiety in the side chains into the corresponding vicinal tricarbonyl moiety. The tricarbonyl moiety was highly reactive with water to permit its rapid conversion into a geminal diol structure in water-containing acetone. On the other hand, heating the resulting polymer bearing the geminal diol structure under vacuum enabled successful recovery of the vicinal tricarbonyl moiety to demonstrate the reversible nature of this system, which allowed us to repeat the hydration-dehydration cycle without deteriorating the polymer structure.

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“…7-Azaisoindigo was rst synthesized in order to provide a more electron decient analogue to isoindigo. While 7-azaisoindigo derivatives have been explored for their use in medicinal chemistry, 38,39 no work has been done to evaluate their utility in optoelectronic applications. The synthesis started from the commercially available 7-azaindole, which was N-alkylated and then oxidized to the corresponding 1-alkyl-7azaisatin.…”

Section: Synthesis Of Donor-acceptor Chromophoresmentioning

confidence: 99%

7-Azaisoindigo as a new electron deficient component of small molecule chromophores for organic solar cells

2014

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The use of 7-azaisoindigo as an electron accepting moiety in donor-acceptor chromophores is reported for the first time. Four chromophores were synthesized that contained either 2,2 0-bithiophene or 3,3 0bis(dodecyloxy)-2,2 0-bithiophene as an electron-donating sub-unit and either isoindigo or 7azaisoindigo as an electron acceptor. The inclusion of a heteroatom in the isoindigo framework was designed to probe its effect on the LUMO, while 3,3 0-bis(dodecyloxy)-2,2 0-bithiophene was used as an electron rich alternative to 2,2 0-bithiophene in order to similarly evaluate its effect on the HOMO level. The electronic properties of the resulting chromophores were fully characterized by UV/visible spectroscopy, cyclic voltammetry, and density functional theory. All four dyes were evaluated for their performance as electron donors in bulk heterojunction solar cells using PC 61 BM as the electron acceptor. Devices that used the isoindigo and 3,3 0-bis(dodecyloxy)-2,2 0-bithiophene-based dye displayed the best performance, reaching a maximum power conversion efficiency of 0.93%.

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An improved preparation of isatins from indoles

Cited by 19 publications

References 9 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Construction of reversible hydration–dehydration system by a model compound and a novel polymer bearing vicinal tricarbonyl structure

7-Azaisoindigo as a new electron deficient component of small molecule chromophores for organic solar cells

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