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Tuning the Chemoselectivity of Dehydroacetic Acid Derived Enones by Isoniazid and Phenylhydrazines: An Efficient Access to 3‐Styryl Pyrano[2,3‐ c ]pyrazolones
Author(s) -
Swarnkar Sumedha,
Ansari Mohd Yeshab,
Kumar Atul
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000748
Subject(s) - chemoselectivity , chemistry , pyrazolones , annulation , dehydroacetic acid , organic chemistry , combinatorial chemistry , stereochemistry , catalysis
The first‐time reported nitrogen source‐based chemoselectivity of dehydroacetic acid (DHA)‐derived enones has been tuned by isoniazid (INH), and phenylhydrazines respectively. When INH a first‐line antitubercular drug, was employed as a new surrogate for nitrogen source, preferentially unconventional 1,3‐dicarbonyl addition occurred, providing a series of fused 3‐styryl pyrano[2,3‐ c ]pyrazolones in good yields. While in the presence of phenylhydrazines and molecular iodine, the reaction was proceeded via oxidative annulation across enone framework, resulting in the efficient and straightforward access to 3‐pyrazolyl pyranones.