Rearrangement of 2-(benzofuran-2-yl)-3-phenylpyridines via photoinduced 6p-electrocyclization

Article Chemistry, Applied

Photoinduced Annulation of N-Phenylbenzamides for the Synthesis of Phenanthridin-6(5H)-Ones

Nana Wang et al.

Summary: A concise method for the synthesis of phenanthridin-6(5H)-ones via photoinduced intramolecular annulation of N-phenylbenzamides was developed. The method is efficient, environmentally friendly, and can be conducted at room temperature.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Article Chemistry, Organic

Photoinduced Skeletal Rearrangement of Diarylethenes: Photorelease of Lewis Acid and Synthetic Applications

Alexey Zakharov et al.

Summary: The study found that skeletal photorearrangement of ortho-halogen-substituted diarylethenes induced by UV light can lead to the formation of bi- or tricyclic frameworks depending on the type of halogen substituent and solvent used. The reaction pathways differ, with bicyclic fused aromatics formed through photocyclization with halogen abstraction, and tricyclic frameworks formed via tandem electrocyclization/sigmatropic shift reactions. Additionally, these compounds can also function as both brominating agents and Lewis acids for catalyzing electrophilic reactions.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Biphenyl Cyclobutenone Photoelectrocyclizations

Changhang Dai et al.

Summary: In this study, it was demonstrated that readily available conjugated bis-aryl cyclobutenones undergo photoelectrocyclization reactions to form the corresponding dihydrophenanthrene cyclobutanones under specific conditions. Additionally, it was found that cyclobutenone electrocyclizations and cyclo-reversions are in equilibrium.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

General approach to substituted naphtho[1,2-b]benzofurans via photochemical 6π-electrocyclization of benzofuranyl containing cinnamonitriles

Boris Lichitsky et al.

Summary: This study presents a method for synthesizing naphtho[1,2-b]benzofurans through a photoinduced reaction, confirming the structures of key intermediates and target products. The research provides valuable insights into the reaction mechanism and synthesis of these compounds.

TETRAHEDRON (2021)

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Article Chemistry, Applied

Synthesis of Trans-4a,12b/3,4-Dihydrodibenzo[f,h]quinolin-2(1H)-Ones and Dibenzo[f,h]quinolin-2(1H)-Ones via Irradiation of 6-Biphenylpyridine-2(1H)-Ones

Jingzhi Sui et al.

Summary: The synthesis of three types of quinoline compounds, including trans-4a,12b-dihydrodibenzo[fh]quinolin-2(1H)-ones (2), dibenzo[f,h]quinolin-2(1H)-ones (3) and 3,4-dihydrodibenzo[f,h]quinolin-2(1H)-ones (4), was achieved through photo-induced annulation of 6-([1,1'-biphenyl]-2-yl)pyridine-2(1H)-ones (1) under 313 nm UV light. The highest yield reached 95%.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Tunable photochemical 6π heterocyclization reactions mediated by a boron Lewis acid

Lishuang Ma et al.

Summary: The study provides a mechanistic insight into the regulation effect of a boron Lewis acid (BF3) on the photochemical 6 pi heterocyclization of a beta-enaminone using multi-configurational ab initio calculations. The computational results reveal that the enaminone's excitation energies and properties can be photochemically tuned in the presence of a BF3 Lewis acid catalyst, allowing for a smooth catalyzed 6 pi heterocyclization on the singlet (1)pi pi* hypersurface.

NEW JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Organic

Synthesis of 6-phenylbenzo[h]quinolines via photoinduced dehydrogenative annulation of (E)-2-phenyl-3-styrylpyridines

Lixin Niu et al.

Summary: The method utilizes UV irradiation to achieve the synthesis of 6-phenylbenzo[h]quinolines without the need for transition metal catalyst and oxidant, offering high atom efficiency and mild reaction conditions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Organic

Synthesis of cis/trans-dihydrochromenones via a photoinduced rearrangement of 4-phenyl-3-aryl/cyclohexenylcoumarins

Wangxi Gao et al.

Summary: A concise and environmentally friendly protocol has been developed for the synthesis of cis-dihydrochromenones and trans-dihydrochromenones in EtOH at room temperature. The described photorearrangement proceeded smoothly without the addition of any transition metals and additives, providing good yields. It is believed that the photorearrangement of 4-phenyl-3-arylcoumarins proceeds via 6 pi-electrocyclization, a [1,3]-hydrogen shift and keto-enol isomerization.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Organic