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[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with diazo compounds and nitrilimines – synthesis of pyrazolines and pyrazoles

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Chemistry of Heterocyclic Compounds Aims and scope

1,3-Dipolar cycloaddition reactions of 3,3,3-trifluoropropene derivatives containing a sulfonyl, sulfamide, or sulfoximine substituent in position 1 with diazomethane proceed with the formation of 3-substituted 4-(trifluoromethyl)-4,5-dihydro-1H-pyrazoles and 3-(trifluoromethyl)-1H-pyrazole, whereas reactions with ethyl diazoacetate and 2,2,2-trifluorodiazoethane lead to the formation of isomeric 5(3)-substituted 4-trifluoromethyl-3,4(4,5)-dihydro-2(1)H-pyrazoles and 4-substituted 5-(trifluoromethyl)-4,5-dihydro-1Hpyrazoles, the stability of which depends on the nature of the heteroatomic substituent. The cycloaddition of 1-sulfonyl- and 1-sulfamoylsubstituted derivatives of 3,3,3-trifluoropropene to C-carbethoxy-N-phenylnitrilimine gives rise to 4-substituted ethyl 1-phenyl-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxylates and ethyl 1-phenyl-4-(trifluoromethyl)-1H-pyrazole-3-carboxylate.

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Notes

  1. Hereinafter in the experimental part, the signals of the major isomer are marked with an asterisk (*), the signals of both isomers are marked with two asterisks (**).

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv, 02660, Ukraine

    Yuriy N. Маrkitanov, Vadim М. Тimoshenko, Sergiy S. Мykhaylychenko, Eduard B. Rusanov & Yuriy G. Shermolovich

  2. L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, 50 Kharkivske Shose, Kyiv, 02160, Ukraine

    Alexandr I. Khyzhan

  3. Enamine Ltd., 78 Chervonotkatska St., Kyiv, 02094, Ukraine

    Alexandr I. Khyzhan

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  1. Yuriy N. Маrkitanov
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  2. Vadim М. Тimoshenko
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Correspondence to Vadim М. Тimoshenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(11), 1107–1115

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Маrkitanov, Y.N., Тimoshenko, V.М., Мykhaylychenko, S.S. et al. [3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with diazo compounds and nitrilimines – synthesis of pyrazolines and pyrazoles. Chem Heterocycl Comp 57, 1107–1115 (2021). https://doi.org/10.1007/s10593-021-03029-8

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