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1 article(s) from Nagła, Karolina

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

Greta Utecht-Jarzyńska,
Karolina Nagła,
Grzegorz Mlostoń,
Heinz Heimgartner,
Marcin Palusiak and
Marcin Jasiński

Beilstein J. Org. Chem. 2021, 17, 1509–1517, doi:10.3762/bjoc.17.108

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Figure 1: Structures of exemplary benzo- and heteroaromatic fused 1,4-quinone drugs and natural products.

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Scheme 1: First [3 + 2]-cycloaddition of 1,4-naphthoquinone (1a) with intermediate nitrile imine 2, generated...

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Scheme 2: Selected applications of trifluoroacetonitrile imines 7 in the synthesis of S-containing 5- and 6-m...

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Scheme 3: Synthesis of [3 + 2]-cycloadducts 9a–l derived from CF₃-substituted nitrile imines 7a–h and 1,4-qui...

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Figure 2: X-ray structure of 3-trifluoromethylpyrazole derivative 9d. The labeling scheme of the asymmetric u...

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Scheme 4: Thermal elimination of MeOH from the initial [3 + 2]-cycloadduct of 1d and nitrile imine 7d generat...

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Scheme 5: Formation of the thermally stable, initially formed [3 + 2]-cycloadduct 10c obtained from 1e and ni...

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Figure 3: Electronic absorption spectra for selected a) naphthoquinone-derived (9c, 9d, 9g) and b) anthraquin...

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Published 28 Jun 2021

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