Synthesis of Xanthones by Daylight Photooxidative Cyclization of (E)-2-Styrylchromones

Silva, Artur M. S.; Tavares, Hilário R.; Cavaleiro, José A. S.

doi:10.1515/hc.1996.2.3.251

Cited by 11 publications

(3 citation statements)

References 2 publications

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“…The Journal of Organic Chemistry The synthetic scope of the photorearrangements of diarylethenes is presented in Scheme 5. Photoreactions of stilbene and styrylheterocycles 15 (Scheme 5A) under anaerobic conditions allow one to synthesize a number of naphthalenes and benzoheterocycles (benzofurans and benzothiophenes), substituted, depending on the structure of 15 and reaction conditions, with butadiene (16) or but-3-en-2-one (17) substituents, or annulated with cyclohexanone (18). This type of photorearrangement occurs in high yields only for stilbenes and their analoges under inert conditions.…”

Section: Methodsmentioning

confidence: 99%

“…Irradiation of diarylethene 11 with a 4 H -chromen-4-one substituent under inert conditions gave naphthalene 12 in a high yield (Scheme ). The photocyclization–oxidation of diarylethene 13 is the closest analogue of this reaction leading to the Mallory product …”

Section: Photolysis Under Inert Conditionsmentioning

confidence: 99%

“…The photocyclization−oxidation of diarylethene 13 is the closest analogue of this reaction leading to the Mallory product. 18 Scheme 2…”

Section: Photolysis Under Inert Conditionsmentioning

confidence: 99%

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Switching the Mallory Reaction to Synthesis of Naphthalenes, Benzannulated Heterocycles, and Their Derivatives

Lvov

2020

J. Org. Chem.

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This review analyzes the new life of a long-known reaction, the photocyclization of diarylethenes, which became a classical tool for the synthesis of phenanthrenes and their heterocyclic analogues (Mallory reaction). It has been shown in recent years that certain diarylethenes undergo photorearrangement to naphthalenes, benzannulated heterocycles, or related products with bicyclic unit. Herein, I analyze how the Mallory reaction path can be altered to obtain bicyclic rather than tricyclic products. The mechanistic aspects and scope of the reaction are discussed.

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Section: Methodsmentioning

confidence: 99%

Section: Photolysis Under Inert Conditionsmentioning

confidence: 99%

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Switching the Mallory Reaction to Synthesis of Naphthalenes, Benzannulated Heterocycles, and Their Derivatives

Lvov

2020

J. Org. Chem.

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Novel ( E )‐ and ( Z )‐2‐Styrylchromones from ( E, E )‐2′‐Hydroxycinnamylideneacetophenones – Xanthones from Daylight Photooxidative Cyclization of ( E )‐2‐Styrylchromones

Silva¹,

Pinto

Tavares

et al. 1998

European J Organic Chem

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The oxidative cyclization of (E,E)‐2′‐hydroxycinnamylideneacetophenones 1a–e, and (E, E)‐2′‐benzyloxy‐6′‐hydroxycinnamylideneacetophenones 1i–l with DMSO/iodine, gave (E)‐2‐styrylchromones 3a–e,i–l. However, in the case of (E, E)‐γ‐alkyl‐2′‐hydroxycinnamylideneacetophenones 1f–h, (E)‐ and (Z)‐2‐styrylchromones 3f–h and 4f–h were obtained. The stereochemistry of the (E,E)‐cinnamylideneacetophenones 1 and (E)‐ and (Z)‐2‐styrylchromones 3 and 4 was established by NOE experiments. The induced daylight photooxidative cyclization of some (E)‐2‐styrylchromones 3a,f–h gave 12H‐benzo[a]xanthene‐12‐ones 6a,f–h.

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New Syntheses of Flavones from Diels–Alder Reactions of 2-Styrylchromones withortho-Benzoquinodimethanes

Silva¹,

Silva

Tomé

et al. 1999

Eur. J. Org. Chem.

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The first reported cycloaddition reactions of 2‐styrylchromones with ortho‐benzoquinodimethane afforded 2‐[2‐(3‐aryl‐1,2,3,4‐tetrahydronaphthyl)]chromones. These cycloadducts were converted into the corresponding 2‐[2‐(3‐arylnaphthyl)]chromones (benzoflavone derivatives) by bromination/dehydrobromination processes. These benzoflavone derivatives were also obtained in one‐pot cycloaddition reactions of 2‐styrylchromones with ortho‐benzoquinodibromomethane.

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Synthesis of Xanthones by Daylight Photooxidative Cyclization of (E)-2-Styrylchromones

Cited by 11 publications

References 2 publications

Switching the Mallory Reaction to Synthesis of Naphthalenes, Benzannulated Heterocycles, and Their Derivatives

Switching the Mallory Reaction to Synthesis of Naphthalenes, Benzannulated Heterocycles, and Their Derivatives

Novel ( E )‐ and ( Z )‐2‐Styrylchromones from ( E, E )‐2′‐Hydroxycinnamylideneacetophenones – Xanthones from Daylight Photooxidative Cyclization of ( E )‐2‐Styrylchromones

New Syntheses of Flavones from Diels–Alder Reactions of 2-Styrylchromones withortho-Benzoquinodimethanes

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