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TEMPO‐Mediated Selective Synthesis of Isoxazolines, 5‐Hydroxy‐2‐isoxazolines, and Isoxazoles via Aliphatic δ ‐C(sp3)‐H Bond Oxidation of Oximes
Author(s) -
Mondal Santanu,
Biswas Sourabh,
Ghosh Krishna Gopal,
Sureshkumar Devarajulu
Publication year - 2021
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202100572
Subject(s) - chemistry , hydrogen atom , selectivity , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , group (periodic table)
Selective synthesis of three different bioactive heterocycles; isoxazolines, 5‐hydroxy‐2‐isoxazolines and isoxazoles from the same starting material using TEMPO (2,2,6,6‐Tetramethylpiperidin‐1‐oxyl) as a radical initiator is reported. Selectivity was achieved using different oxidants with TEMPO. The reaction goes through a 1,5‐HAT (hydrogen atom transfer) process resulting in products with good yields. This strategy offers a straightforward route to three different heterocycles from oximes via radical‐mediated C( sp 3 )‐H oxidation.