Acid-promoted cleavage of the C–C double bond of N-(2-Hydroxylphenyl)enaminones for the synthesis of benzoxazoles

Ge, Bailu; Peng, Yanling; Liu, Jing; Wen, Shengyou; Peng, Cheng; Cheng, Guolin

doi:10.1016/j.tet.2019.130818

Cited by 10 publications

(28 citation statements)

References 45 publications

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“…1 H NMR (400 MHz, CDCl 3 ) δ 7.74−7.62 (m, 2H), 7.52−7.40 (m, 3H), 7.00−6.80 (m, 4H), 4.37 (s, 1H). 19 F NMR (376 MHz, CDCl 3 ) δ −84.3 (s).…”

Section: ■ Conclusionmentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ) δ 7.72−7.62 (m, 2H), 7.50−7.42 (m, 3H), 6.78 (s, 1H), 6.75 (d, J = 7.6 Hz, 1H), 6.65 (d, J = 7.6 Hz, 1H), 4.25 (s, 1H), 2.30 (s, 3H). 19 F NMR (376 MHz, CDCl 3 ) δ −84.3 (s). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 150.6, 135.2, 133.1, 133.0, 129.9, 128.8, 125.8 (q, J = 1.0 Hz), 123.0 (q, J = 288.9 Hz), 122.1, 112.5, 109.5, 98.0 (q, J = 32.3 Hz), 21…”

Section: ■ Conclusionmentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ) δ 7.71−7.61 (m, 2H), 7.53−7.42 (m, 3H), 6.77 (dd, J = 8.4, 4.8 Hz, 1H), 6.71 (dd, J = 8.4, 2.4 Hz, 1H), 6.60−6.51 (m, 1H), 4.25 (s, 1H). 19 F NMR (376 MHz, CDCl 3 ) δ −84.4 (s), −119.5 (s). 13 6-Chloro-2-phenyl-2-(trifluoromethyl)-2,3-dihydrobenzo[d]oxazole (1d).…”

Section: ■ Conclusionmentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ) δ 7.70−7.60 (m, 2H), 7.54−7.41 (m, 3H), 7.19 (d, J = 8.0 Hz, 1H), 7.05 (s, 1H), 6.98 (d, J = 8.0 Hz, 1H), 4.54 (s, 1H). 19 F NMR (376 MHz, CDCl 3 ) δ −62.1 (s), −84.4 (s). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 152.7, 136.3, 134.4, 130.3, 129.0, 125.6 (q, J = 1.0 Hz), 124.8 (q, J = 33.3 Hz), 124.1 (q, J = 272.7 Hz), 122.6 (q, J = 288.9 Hz), 120.7 (q, J = 4.0 Hz), 109.1 (q, J = 4.0 Hz), 108.3, 98.7 (q, J = 33.3 Hz).…”

Section: ■ Conclusionmentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ) δ 7.71−7.61 (m, 2H), 7.53−7.40 (m, 3H), 6.82 (dd, J = 8.4, 4.0 Hz, 1H), 6.66− 6.44 (m, 2H), 4.49 (s, 1H). 19 F NMR (376 MHz, CDCl 3 ) δ −84.4 (s), −121.8 (s). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 158.4 (d, J = 239.4 Hz), 146.2 (d, J = 2.0 Hz), 136.6 (d, J = 12.1 Hz), 134.8, 130.1, 128.9, 125.6 (q, J = 1.0 Hz), 122.8 (q, J = 289.9 Hz), 108.2 (d, J = 10.1 Hz), 107.8 (d, J = 25.3 Hz), 100.8 (d, J = 29.3 Hz), 98.5 (q, J = 33.3 Hz).…”

Section: ■ Conclusionmentioning

confidence: 99%

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Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF₃ Process

et al. 2021

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An unexpected cleavage of the C sp3 –CF3 bond of CF3-hydrobenzoxazoles has been disclosed, affording a range of 2-aryl benzoxazoles under metal-free and redox-neutral conditions. This transformation has demonstrated broad substrate scope and good compatibility of functional groups. 2-Aryl benzothiazole and 2-aryl benzoimidazole could be smoothly assembled in the same manner. On the basis of preliminary mechanistic studies, base initiated and aromatization driven β-carbon elimination was considered to be the key step for the formation of 2. This reaction offers an alternative, facile, and sustainable route to access important 2-aryl benzoxazole motifs.

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“…1 H NMR (400 MHz, CDCl 3 ) δ 7.74−7.62 (m, 2H), 7.52−7.40 (m, 3H), 7.00−6.80 (m, 4H), 4.37 (s, 1H). 19 F NMR (376 MHz, CDCl 3 ) δ −84.3 (s).…”

Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

See 3 more Smart Citations

Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF₃ Process

et al. 2021

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Base‐Promoted Cascade C−N and C−C Formation: An Approach to Pyrido[1,2‐a]pyrimidinones from Ynones and 2‐Methylpyrimidin‐4‐ols

Tan

Yao

et al. 2022

Asian J Org Chem

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An efficient base-promoted approach for the synthesis of pyrido[1,2-a]pyrimidinones from ynones and 2methylpyrimidin-4-ols have been developed via the CÀ N and CÀ C formation procedure. Diversely structural pyrido[1,2a]pyrimidinones were afforded in up to 95% yield for 29 examples. This reaction featured with advantages such as practical tandem procedure, wide functional group tolerance and metal-free conditions, which has potential application in synthetic and medicinal chemistry.

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Acid‐Promoted Carbon‐Carbon Triple Bond Cleavage of Ynones for the Synthesis of Benzo[d]oxazoles/Benzo[d]thiazoles and 1‐Arylethan‐1‐ones

Guo

et al. 2022

Eur J Org Chem

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A synchronous synthesis of benzo [d]oxazoles/benzo [d]thiazoles and 1-arylethan-1-ones enabled by acid-promoted CÀ C triple bond cleavage of ynones is disclosed. This reaction was accomplished with good tolerance of various functional groups and aminophenols/aminobenzenethiols to access the corre-sponding products, especially some structurally special 1arylethan-1-ones, in moderate to good yield. Furthermore, the readily accessible synthesis of some biologically active molecules has highlighted the synthetic utility of this strategy.

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Acid-promoted cleavage of the C–C double bond of N-(2-Hydroxylphenyl)enaminones for the synthesis of benzoxazoles

Cited by 10 publications

References 45 publications

Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF₃ Process

Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF₃ Process

Base‐Promoted Cascade C−N and C−C Formation: An Approach to Pyrido[1,2‐a]pyrimidinones from Ynones and 2‐Methylpyrimidin‐4‐ols

Acid‐Promoted Carbon‐Carbon Triple Bond Cleavage of Ynones for the Synthesis of Benzo[d]oxazoles/Benzo[d]thiazoles and 1‐Arylethan‐1‐ones

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Acid-promoted cleavage of the C–C double bond of N-(2-Hydroxylphenyl)enaminones for the synthesis of benzoxazoles

Cited by 10 publications

References 45 publications

Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF3 Process

Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF3 Process

Base‐Promoted Cascade C−N and C−C Formation: An Approach to Pyrido[1,2‐a]pyrimidinones from Ynones and 2‐Methylpyrimidin‐4‐ols

Acid‐Promoted Carbon‐Carbon Triple Bond Cleavage of Ynones for the Synthesis of Benzo[d]oxazoles/Benzo[d]thiazoles and 1‐Arylethan‐1‐ones

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Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF₃ Process

Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF₃ Process