Photoinduced homolytic C–H activation in<i>N</i>-(4-homoadamantyl)phthalimide

Cindro, N.; Horvat, Margareta; Mlinarić‐Majerski, Kata; Griesbeck, Axel G.; Basarić, Nikola

doi:10.3762/bjoc.7.36

Cited by 6 publications

(8 citation statements)

References 47 publications

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“…The -abstraction gives rise to a 1,5-biradical (1,5BR) that undergoes stereoselective cyclization to furnish the major product, exo-alcohol 32 (Scheme 1.14) [22]. The observed selectivity of the 1,5-cyclization is in line with the stability of the product formed.…”

Section: 9)mentioning

confidence: 95%

“…In all investigated solvents, exo-alcohol 32 was the major product. The photochemical reaction was more efficient in solvent system containing acetone rather than MeCN [22]. However, prolonged irradiation in Me 2 CO-H 2 O (18 h) gave only alcohol 32 which was isolated in 53% yield [22].…”

Section: 9)mentioning

confidence: 98%

“…A case of the photoinduced regioselective H-abstraction and the stereoselective cyclization of the 1,5-biradical was explored recently with N-(4-homoadamantyl)phthalimide (31) as substrate in aqueous media [22].…”

Section: 9)mentioning

confidence: 99%

“…Irradiation of 31 (Scheme 1.13) was performed in MeCN, MeCN-H 2 O (3:1), Me 2 CO and Me 2 CO -H 2 O (3:1) and gave three products, i.e., the exo-alcohol 32, and the azepinediones syn-33 and anti-33 (Scheme 1.13) [22]. In all investigated solvents, exo-alcohol 32 was the major product.…”

Section: 9)mentioning

confidence: 99%

“…The major product, exo-alcohol 32 was a result of the regioselective H-abstraction and the stereoselective cyclization of the 1,5-biradical, Scheme 1.13, and 1.14 [22]. Products 33 arise from -H abstraction and formation of 1,4-biradicals, as shown in Scheme 1.14 [22].…”

Section: 9)mentioning

confidence: 99%

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Photoinduced Cyclization Reactions in Aqueous Media

Martin-Flesia¹,

Postigo²

2012

COC

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This account intends to cover recent literature on photoinduced cyclization reactions in water or aqueous media. The reactions covered do not proceed by the assistance of metals, or through electron transfer reactions mediated by metallic species or complexes. Radical cyclization of perfluoroalkyl-substituted compounds is neither the subject of this article, since these examples have been reviewed recently. Instead, photomacrocyclization and photoelectrocyclic ring closure reactions are the aims of this article, as well as the syntheses of lactones and 5-methyleneoxazolidin-4-ones, showing the scope of these reactions carried out in an environmentally-friendly media. These cyclization reactions will be shown to enable the syntheses of important synthetic targets, with relevancy in biochemistry and medicinal chemistry.

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Section: 9)mentioning

confidence: 95%

Section: 9)mentioning

confidence: 98%

Section: 9)mentioning

confidence: 99%

Section: 9)mentioning

confidence: 99%

Section: 9)mentioning

confidence: 99%

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Photoinduced Cyclization Reactions in Aqueous Media

Martin-Flesia¹,

Postigo²

2012

COC

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Antiproliferative and Antiviral Activity of Three Libraries of Adamantane Derivatives

Basarić

Sohora

Cindro

et al. 2014

Archiv der Pharmazie

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Three libraries of adamantane derivatives were synthesized and evaluated for antiviral and antiproliferative activities against a broad variety of DNA and RNA viruses. Whereas none of the compounds exhibit antiviral activity at subtoxic concentrations, antiproliferative activity was found against murine leukemia cells (L1210), human T-lymphocyte cells (CEM), and cervix carcinoma cells (HeLa) for 4, 8, and 10.

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Photoinduced H‐Abstraction in Homo‐ and Protoadamantylphthalimide Derivatives in Solution and in Organized and Constrained Media

et al. 2013

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The photochemical reactivity of homoadamantylphthalimide 5 and protoadamantylphthalimides 9 and 10 was investigated in solution, in the β‐cyclodextrin (CD) complex, and in the solid state. The triplet excited states of 5, 9 and 10 were characterized by laser flash photolysis. Sensitized irradiation in solution was found to give rise to polycyclic products through a transiently generated higher excited triplet state, not detectable by LFP. Direct excitation of 5, 9 and 10 gives, in addition to the products arising from the triplet state, cleavage products probably generated through a singlet state. Complexation with β‐cyclodextrin changes the regiochemistry of H‐abstraction. In the solid state, 5 and 9 are both photoreactive though state‐dependent product mixtures are noted. Irradiation of 5 affords only one product whereas irradiation of 9 affords the same product mixture regardless of whether irradiation is performed in the solid state or in CH3CN solution.

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Photoinduced homolytic C–H activation inN-(4-homoadamantyl)phthalimide

Cited by 6 publications

References 47 publications

Photoinduced Cyclization Reactions in Aqueous Media

Photoinduced Cyclization Reactions in Aqueous Media

Antiproliferative and Antiviral Activity of Three Libraries of Adamantane Derivatives

Photoinduced H‐Abstraction in Homo‐ and Protoadamantylphthalimide Derivatives in Solution and in Organized and Constrained Media

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