A Rearrangement of 4-Phenylbenzo[d]oxazoles to Phenanthridin-4-ols

Fisyuk, Alexander S.; Shatsauskas, Anton L.; Keyn, Ekaterina S.; Stasyuk, Anton J.; Kirnosov, Sergey A.; Shuvalov, Vladislav Yu.; Kostyuchenko, Anastasia S.

doi:10.1055/a-2193-5593

Synthesis

2023

DOI: 10.1055/a-2193-5593

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A Rearrangement of 4-Phenylbenzo[d]oxazoles to Phenanthridin-4-ols

Alexander S. Fisyuk,

Anton L. Shatsauskas,

Ekaterina S. Keyn

et al.

Abstract: A new approach was developed for the synthesis of phenanthridin-4-ols and 4-hydroxyphenanthridin-6(5H)-one derivatives in 43–89% yields based on the AlCl3-mediated rearrangement of available 4-phenylbenzo[d]oxazoles and 4-phenyl-1,3-benzoxazol-2(3H)-one. The quantum chemical calculations were used to describe the mechanism and predict the thermodynamic parameters of the reaction under study.

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Cited by 4 publications

References 90 publications

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Oxidative cyclization of N-(2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)thioureas to 7-phenyloxazolo[5,4-b]pyridin-2-amines

Kirnosov,

Shatsauskas,

Zheleznova

et al. 2024

Russ Chem Bull

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Oxidative cyclization of N-(2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)thioureas to 7-phenyloxazolo[5,4-b]pyridin-2-amines

Kirnosov,

Shatsauskas,

Zheleznova

et al. 2024

Russ Chem Bull

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New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones

Fisyuk,

Shuvalov,

Shatsauskas

et al. 2023

Synthesis

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Reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole with azlactones under solvent-free conditions with heating furnished tetrahydro-1H-pyrazolo[3,4-b]pyridines. The latter were converted to oxazolo[5,4-b]pyrazolo[4,3-e]pyridines by the action with POCl3 on air. Further reaction of oxazolo[5,4-b]pyrazolo[4,3-e]pyridines with hydrazine hydrate and alkali led to the formation of 5-amino-1,7-dihydro-6H-pyrazolo[3,4-b]pyridin-6-ones, which reacted with aluminum chloride to yield 3,4-dihydro-5H-pyrazolo[4,3-f][1,7]naphthyridin-5-ones. Some of the synthesized compounds show antioxidant activity or are effective phosphors.

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Synthesis of Dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: The Pictet–Spengler Reaction versus a Rearrangement of 4-Phenyl[1,3]oxazolo[4,5-c]quinolines

Fisyuk,

Shatsauskas,

Kirnosov

et al. 2024

Synthesis

Self Cite

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Two approaches were proposed to the synthesis of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones. The one-step method based on the Pictet–Spengler reaction of 3-amino-2-phenylquinolin-4(1H)-one with aromatic aldehydes requires heating in a strong acidic media, which leads to significant limitations on the possible products. The second approach is based on the conversion of 3-amino-2-phenylquinolin-4(1H)-one to 4-phenyl[1,3]oxazolo[4,5-c]quinolines followed by rearrangement under the action of AlCl3. A significant advantage of the two-step synthesis is the possibility of obtaining a wider range of dibenzo[b,h][1,5]naphthyridin-7(12H)-ones, including those not available using the Pictet–Spengler reaction.

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A Rearrangement of 4-Phenylbenzo[d]oxazoles to Phenanthridin-4-ols

Cited by 4 publications

References 90 publications

Oxidative cyclization of N-(2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)thioureas to 7-phenyloxazolo[5,4-b]pyridin-2-amines

Oxidative cyclization of N-(2-oxo-4-phenyl-1,2-dihydropyridin-3-yl)thioureas to 7-phenyloxazolo[5,4-b]pyridin-2-amines

New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones

Synthesis of Dibenzo[b,h][1,5]naphthyridin-7(12H)-ones: The Pictet–Spengler Reaction versus a Rearrangement of 4-Phenyl[1,3]oxazolo[4,5-c]quinolines

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