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

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...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2017-02, Vol.53 (2), p.156-160
Main Authors: Suzdalev, Konstantin F., Krachkovskaya, Alina V., Kletskii, Mikhail E., Burov, Oleg N., Tatarov, Artem V., Kurbatov, Sergey V.
Format: Article
Language:English
Subjects:
Ammonium acetate
Chemistry
Chemistry and Materials Science
Ethanol
Organic Chemistry
Pharmacy
Quantum chemistry
Resveratrol
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-017-2033-9