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Unexpected pyrylium to pyrylium domino transformation. Synthesis of pyrano[3,4-c]pyran-7-ium cation and its recyclization to 2,7-naphthyridine derivative

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Chemistry of Heterocyclic Compounds Aims and scope

4-Ethyl-3-formyl-2,6-diphenylpyrylium perchlorate was obtained from 2,6-diphenylpyrylium perchlorate in three steps. Its reaction with triethyl orthoformate was accompanied by rearrangement of the initial pyrylium ring and led to pyrano[3,4-c]pyran-7-ium perchlorate system through a domino process involving ethanol addition-elimination. A plausible mechanism of the reaction is suggested on the basis of DFT quantum-chemical calculations. Reaction of the obtained pyrano[3,4-c]pyran-7-ium perchlorate with ammonium acetate led to a 2,7-naphthyridine derivative without a skeletal rearrangement.

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This work was accomplished with financial support from the Russian Science Foundation (RSF), project No. 14-13-00103.

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Authors and Affiliations

  1. Department of Chemistry, Southern Federal University, 7 Zorge St, Rostov-on-Don, 344090, Russia

    Konstantin F. Suzdalev, Alina V. Krachkovskaya, Mikhail E. Kletskii, Oleg N. Burov, Artem V. Tatarov & Sergey V. Kurbatov

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  1. Konstantin F. Suzdalev
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  2. Alina V. Krachkovskaya
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  3. Mikhail E. Kletskii
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  4. Oleg N. Burov
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  5. Artem V. Tatarov
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  6. Sergey V. Kurbatov
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Corresponding author

Correspondence to Alina V. Krachkovskaya.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(2), 156–160

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Suzdalev, K.F., Krachkovskaya, A.V., Kletskii, M.E. et al. Unexpected pyrylium to pyrylium domino transformation. Synthesis of pyrano[3,4-c]pyran-7-ium cation and its recyclization to 2,7-naphthyridine derivative. Chem Heterocycl Comp 53, 156–160 (2017). https://doi.org/10.1007/s10593-017-2033-9

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  • DOI: https://doi.org/10.1007/s10593-017-2033-9

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