Journal
RSC ADVANCES
Volume 4, Issue 16, Pages 8300-8307Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ra46129g
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- University of Calcutta
- CSIR, New Delhi, India [09/028(0792)/2010 EMR-I]
- U. G. C., New Delhi, India
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A highly efficient and general protocol has been developed for the facile synthesis of highly diversified 1,3,5-trisubstituted pyrazoles and 3,5-disubstituted 2-isoxazolines through one-pot tandem intermolecular, as well as intramolecular, dipolar [3 + 2] cycloaddition reactions. Chemoselective oxidation of aldohydrazone to nitrile imine and aldoximes to nitrile oxides by iodosobenzene in neutral aqueous media was performed. The scope of the reactions in regiocontrolled dipolar cycloaddition with olefins in the presence of PhIO toward highly substituted pyrazole and isoxazoline derivatives has been demonstrated. SDS converted the initially floating reaction mass and the organo-oxidant PhIO into a homogeneous mixture, which on stirring became a turbid emulsion. The micellar arrangement was confirmed by dynamic light scattering and optical microscopy. The new, green and metal free synthetic method enabled the execution of regiocontrolled tandem cycloaddition oxidation sequences leading to a library of pyrazole and isoxazoline derivatives.
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