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Hypervalent Iodine‐Promoted Aromatization Of Exocyclic β‐Enaminones For The Synthesis Of Meta‐N,N‐Diarylaminophenols

Dhananjay Bhattacherjee, Vandna Thakur, Arun K. Shil, Pralay Das
Published 2017 · Chemistry

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A metal- and additive-free milder cascade approach for the synthesis of meta-N,N-diarylaminophenols (DAAP) starting from exocyclic β-enaminones has been developed. The feasibility of the process is rationalized by the suitable molecular geometry of β-enaminones for tandem N-arylative α-iodination and aromatization under milder basic conditions. Furthermore, the developed strategy has been extended to the synthesis of meta-N-benzyl-N-arylaminophenols (BAAP). 4-Ethylpropionyl-2-cyclohexenone has been explored to give 7-diarylaminochroman-2-one (DAAC) by employing a similar one-pot approach. The plausible mechanistic steps were deduced based upon isolation of a stable intermediate and structural identification through X-ray crystallographic analysis.
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