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- Title
Reaction of Norfluorocurarine and 12-Hydroxynorfluorocurarine with Phenylhydrazine.
- Authors
Adizov, Sh. M.; Bruskov, V. P.; Tashkhodzhaev, B.; Khandamov, B. N.; Yuldashev, P. Kh.
- Abstract
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.
- Subjects
PHENYLHYDRAZINE; INDOLE alkaloids; INDOLE; MICHAEL reaction; CRYSTAL structure; INDOLINE
- Publication
Chemistry of Natural Compounds, 2021, Vol 57, Issue 6, p1056
- ISSN
0009-3130
- Publication type
Article
- DOI
10.1007/s10600-021-03549-x