The reaction of the indoline alkaloid 12-hydroxynorfluorocurarine with phenylhydrazine produced 1,2-seco-12-hydroxynorfluorocurarine-2,17-phenylhydrazone, the structure of which was established by an X-ray crystal structure analysis. The proposed mechanism of formation of N was confirmed by quantum-mechanical calculations. The reaction was shown to proceed via a Michael mechanism with phenylhydrazine N atoms adding to C2 and C17 of the alkaloid to form a pyrazole ring and cleave the indole N1–C2 bond. Quantum-chemical calculations using the product from the reaction of 12-hydroxynonrfluorocurarine and phenylhydrazine as an example explained the proposed mechanism.
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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2021, pp. 905–909.
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Adizov, S.M., Bruskov, V.P., Tashkhodzhaev, B. et al. Reaction of Norfluorocurarine and 12-Hydroxynorfluorocurarine with Phenylhydrazine. Chem Nat Compd 57, 1056–1061 (2021). https://doi.org/10.1007/s10600-021-03549-x
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DOI: https://doi.org/10.1007/s10600-021-03549-x