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Base Catalyzed Scaffold Shift from Pyranone Carboxamide to Pyrazolyl Acetamide through Intramolecular Ring Transformation
Author(s) -
Rozy Farhana,
Sharon Ashoke
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900373
Subject(s) - acetamide , intramolecular force , ring (chemistry) , chemistry , carboxamide , combinatorial chemistry , scaffold , stereochemistry , organic chemistry , computer science , database
Scaffold shift of biologically active pyranone carboxamide to pyrazolyl acetamide, which is another biologically important scaffold was achieved through one‐pot base catalyzed metal‐free intramolecular ring transformation. Out of the two probable mechanistic pathways (Figure 3), substitution at C‐4 by hydrazineyl leading to a pyranone intermediate followed by an intramolecular attack of hydrazineyl at C‐6 and decarboxylation to yield pyrazolyl acetamides was rationalized through LCMS, UV monitoring and computational studies.