Advanced Synthesis and Catalysis p. 2202 - 2208 (2017)
Update date:2022-08-03
Topics: Synthesis Aromatization Hypervalent Iodine Exocyclic β-Enaminones meta-N,N-Diarylaminophenols
Bhattacherjee, Dhananjay
Thakur, Vandna
Shil, Arun K.
Das, Pralay
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. (Figure presented.).
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