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Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif

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Chemistry of Heterocyclic Compounds Aims and scope

An effective method was developed for the synthesis of 1,3,5-trisubstituted pyrazoles by using acetylenic ketones, obtained from ethyl 5-ethynylanthranilate, in reactions with substituted hydrazines and hydrazides. It was shown that the cyclization of ethyl 5-(3-aryl-3-oxopropinyl)- anthranilates with arylhydrazines proceeded regioselectively and led to the formation of 1,3,5-trisubstituted pyrazoles containing an anthranilate moiety at the position С-3. Significant deterioration of regioselectivity was observed in the reactions of ethyl 5-(3-aryl-3-oxopropinyl)anthranilates with N-methyl- and N-tert-butylhydrazines. The initial products formed in reactions of ethyl 5-[3-(4-fluorophenyl)-3-oxopropinyl]anthranilate with benzoyl and isonicotinoyl hydrazides were 5-hydroxypyrazolines, which underwent dehydration in the presence of pyridine and thionyl chloride in benzene, giving the respective 1,3,5-trisubstituted pyrazoles.

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ACKNOWLEDGEMENT

This work received financial support from the Russian Science Foundation (grant 18-13-00361).

The analytical and spectral studies were performed at the Collective Use Center for chemical studies at the Siberian Branch of the Russian Academy of Sciences.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russia

    Viktor A. Savel’ev, Anna A. Kotova, Tatyana V. Rybalova & Elvira E. Shults

  2. Novosibirsk State University, 1 Pirogova St., Novosibirsk, 630090, Russia

    Anna A. Kotova, Tatyana V. Rybalova & Elvira E. Shults

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  1. Viktor A. Savel’ev
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  2. Anna A. Kotova
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  3. Tatyana V. Rybalova
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  4. Elvira E. Shults
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Correspondence to Elvira E. Shults.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(10), 943–955

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Savel’ev, V.A., Kotova, A.A., Rybalova, T.V. et al. Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif. Chem Heterocycl Comp 55, 943–955 (2019). https://doi.org/10.1007/s10593-019-02561-y

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