Hypervalent Iodine‐Promoted Aromatization of Exocyclic β‐Enaminones for the Synthesis of meta‐N, N‐Diarylaminophenols. Issue 13 (4th May 2017)

• Record Type: Journal Article
• Authors: Bhattacherjee, Dhananjay; Thakur, Vandna; Shil, Arun K.; Das, Pralay
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 13(2017)
• Page Start: 2202
• Page End: 2208
• Publication Date: 2017-05-04
• Subjects: aromatization -- β-enaminones -- hypervalent iodine reagents -- metal-free reaction -- triarylamines; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201700004
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :