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. 2022 Aug 31;20(34):6879-6889.
doi: 10.1039/d2ob01282k.

Copper(II)-catalyzed oxidative ipso-annulation of N-arylpropiolamides and biaryl ynones with 1,3-diketones: construction of diketoalkyl spiro-trienones

Chada Raji Reddy  1   2 , Dattahari H Kolgave  1   2 , Uprety Ajaykumar  1   2 , Remya Ramesh  1   2
Affiliations

Copper(II)-catalyzed oxidative ipso-annulation of N-arylpropiolamides and biaryl ynones with 1,3-diketones: construction of diketoalkyl spiro-trienones

Chada Raji Reddy et al. Org Biomol Chem. .

Abstract

An unprecedented copper-catalyzed ipso-annulation reaction of N-(p-methoxyaryl)propiolamides with 1,3-diketones has been developed, which enables the assembly of diketoalkylated spiro[4.5]trienones involving oxidative dearomatization in the presence of ammonium persulfate [(NH4)2S2O8] as the oxidant. This protocol was extended to biaryl ynones, efficiently affording the diketoalkylated spiro[5.5]trienones in good yields. The significance of the diketoalkyl functionality has been illustrated by further transformation into 3-pyrazoyl spiro-trienone, a structurally unique motif.

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