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An Effect of H‐bonding in Synthesis of 1, 5‐Diketones via Tandem Aldol‐Michael Addition Reaction Using Room Temperature Ionic Liquid (RTIL).
Author(s) -
Kamble Sujit S.,
Shankarling Ganapati S.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700034
Subject(s) - acetophenone , ionic liquid , chemistry , aldehyde , yield (engineering) , aldol reaction , hydrogen bond , solvent , chalcone , tandem , michael reaction , reactivity (psychology) , catalysis , hydroxide , organic chemistry , combinatorial chemistry , molecule , materials science , metallurgy , composite material , medicine , alternative medicine , pathology
A simple and convenient protocol for the tandem synthesis of 1,5‐diketone via chalcone intermediate from aldehyde and acetophenone using biodegradable choline hydroxide (ChOH), a Room Temperature Ionic Liquid (RTIL) and effect of hydrogen bonding is described. The mechanistic investigation for unusual reactivity of 10‐propyl‐10H‐phenothiazine‐3‐carbaldehyde with o ‐hydroxy acetophenone showed involvement of the H‐bonding. Shorter reaction time, easy work up and comparably good yield of desired product are crucial features of this methodology which make it an alternative to the other approaches. The ionic liquid used here serves both as catalyst as well as solvent.