Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions

Abstract

Highly stereoselective synthesis of Z-enaminones bearing reactive secondary amino group has been successfully performed in water using tertiary amino group functionalized enaminones under ambient conditions. An interesting promotion effect of water on the reaction via hydrolysis–dehydration condensation has been observed through a designed isotope labeling experiment.

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GRAPHICAL ABSTRACT

Keywords:

• Enaminone
• green synthesis
• mechanism
• multicomponent
• water promotion

ACKNOWLEDGMENTS

Financial support from NSFC of China (No. 21102059), NSF Program of Jiangxi Province (No. 20114BAB213005), and Sponsored Program for Cultivating Youths of Outstanding Ability in Jiangxi Normal University is gratefully acknowledged.

Notes

^a General reaction conditions: 0.3 mmol 1a and 0.3 mmol aniline in 1.5 mL water, stirred at rt for 2 h.

^b Isolated yield.

^a Reaction conditions: 0.3 mmol 1 and 0.3 mol 2, 20 mol% FeCl₃ in 1.5 mL water, stirred at rt for 2 h.

^b Isolated yield.