Visible‐Light‐Promoted Selenylative Spirocyclization of Indolyl‐ynones toward the Formation of 3‐Selenospiroindolenine Anticancer Agents

Zhou, Xiu-Jie; Liu, Hao-Yang; Mo, Zu‐Yu; Ma, Xiangyi; Chen, Yanyan; Tang, Hai‐Tao; Pan, Ying‐Ming; Xü, Yanli

doi:10.1002/asia.202000298

Cited by 64 publications

(42 citation statements)

References 36 publications

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“…All these advantages have meant that in the last seven years there has been a significant increase in the number of works reporting the use of photochemistry in the seleno-functionalization of several classes of organic substrates [ 70 ]. For example, the carbon-selenium bond formation in heteroarene-like indoles [ 71 , 72 ], imidazo[1,2 a ]pyridines [ 73 , 74 ], coumarines [ 75 ], benzothiazoles [ 76 ] and pyridines [ 77 ]; selenylation of naphthols [ 78 ], terminal alkenes [ 79 , 80 ] and alkynes [ 81 , 82 ] and sp 3 carbons [ 83 , 84 ]; and selenocyclization reactions have been reported [ 85 , 86 ]. In these protocols, in general, the substrate, the selenylating reagent and the photocatalyst are stimulated by visible light irradiation via single electron transfer (SET) reactions.…”

Section: Application Of Non-conventional Energy Sources In Organosele...mentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

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Organoselenium compounds have been successfully applied in biological, medicinal and material sciences, as well as a powerful tool for modern organic synthesis, attracting the attention of the scientific community. This great success is mainly due to the breaking of paradigm demonstrated by innumerous works, that the selenium compounds were toxic and would have a potential impact on the environment. In this update review, we highlight the relevance of these compounds in several fields of research as well as the possibility to synthesize them through more environmentally sustainable methodologies, involving catalytic processes, flow chemistry, electrosynthesis, as well as by the use of alternative energy sources, including mechanochemical, photochemistry, sonochemical and microwave irradiation.

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Section: Application Of Non-conventional Energy Sources In Organosele...mentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

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“…Recently, Zhou and coworkers reported a similar selenylative, dearomative cascade cyclization using the indolyl‐ynones 188 [75] . The scope of the reaction allowed functionalization at the indole core or in the alkyne moiety, as in the diaryl disselenide 11 with electron‐donating and withdrawing groups, resulting in the 3‐selenospiroindolenines derivatives 189 in moderate to high yields (up to 90 %).…”

Section: Spirocyclizationmentioning

confidence: 99%

“…Under an oxidizing atmosphere, the peroxidation of the spiro intermediate 184 generates the peroxide radical specie 185 followed by elimination of the OH radical affords the respective spirocompound 186 (Scheme 45). [72–75] The absence of the formation of bis ‐arylselenyl olefins is related to the faster intramolecular reaction rather than the intermolecular reaction with another selenyl radical.…”

Section: Spirocyclizationmentioning

confidence: 99%

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances

Rafique

Rampon

Azeredo

et al. 2021

The Chemical Record

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Organoselenium compounds constitute an important class of substances with applications in the biological, medicinal and material sciences as well as in modern organic synthesis, attracting considerable attention from the scientific community. Therefore, the construction of the C−Se bond via facile, efficient and sustainable strategies to access complex scaffolds from simple substrates are an appealing and hot topic. Visible light can be regarded as an alternative source of energy and is associated with environmentally‐friendly processes. Recently, the use of visible‐light mediated seleno‐functionalization has emerged as an ideal and powerful route to obtain high‐value selenylated products, with diminished cost and waste. This approach, involving photo‐excited substrates/catalyst and single‐electron transfer (SET) between substrates in the presence of visible light has been successfully used in the versatile and direct insertion of organoselenium moieties in activated and unactivated C(sp3)−H, C(sp2)−H, C(sp)−H bonds as well as C−heteroatom bonds. In most cases, ease of operation and accessibility of the light source (LEDs or commercial CFL bulbs) makes this approach more attractive and sustainable than the traditional strategies.

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“…Most of the obtained heterocycles 187 showed in vitro anticancer activity against tumor cell lines MGC-803, HpeG-2, T-24 and HeLa. [230] The method for the formation of the dihydropyrrolidine ring by cleavage of the NÀ O bond of oxime esters upon heating with salts of heavy metals [231] has also been successfully applied to obtain spirocyclic molecules. These transformations are a successful development of the previously described closely related non-catalytic transformations, [232] that Cu(acac) 2 was the most efficient catalyst for this transformation.…”

Section: The Indole Dearomatization Strategy In the Synthesis Of Spirmentioning

confidence: 99%

“…The reaction product 187 was not obtained using dimethyl selenide either ( Scheme 48). Most of the obtained heterocycles 187 showed in vitro anticancer activity against tumor cell lines MGC‐803, HpeG‐2, T‐24 and HeLa [230] …”

Section: Syntheses Of Spiroheterocycles From 3‐alkylidene‐indol‐2‐onementioning

confidence: 99%

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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The review covers the results of studies published in the literature on the synthesis of spiro-linked heterocycles of the indole, quinoline, benzoxazine, benzothiazine, indenoquinoxaline, pyridopyrimidine, and acridine series. Possible approaches to the synthesis of spirocycles through a sequence of well-known Knoevenagel, Michael reactions, deamination cyclization of 1,2-dicarbonyl, CH-acid compounds, direct cycloaddition of activated olefins to isatins, 3-alkylideneindoles, 2-oxindoles, in situ generated azomethine ylides, indenoquinoxalines are analyzed. Attention is drawn to approaches to the preparation of spiro-fused compounds using reactions of intra-and intermolecular dearomatization of indoles. Recent advances in the synthesis of spiro-linked benzo heterocycles from derivatives of 2-olefin substituted anilines are summarized. The examples of the synthesis of spiro-fused heterocycles by means of metal complexes catalyzed decomposition of diazo compounds are given. Some syntheses of biologically active representatives are shown, as well as the use of transformations of spiroheterocycles in the preparation of other heterocycles.

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Visible‐Light‐Promoted Selenylative Spirocyclization of Indolyl‐ynones toward the Formation of 3‐Selenospiroindolenine Anticancer Agents

Cited by 64 publications

References 36 publications

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

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