Synthesis of novel 2-(2,2,2-trifluoro-1-aryl-ethylidene)cyclohexane-1,3-dione: Scaffolds for reagent-based diversity-oriented synthesis

Abstract

Herein, we report the first synthesis and characterization of 2-(2,2,2-trifluoro-1-aryl-ethylidene)cyclohexane-1,3-dione (4a–4t, upto 80%) via a two-step procedure starting from 1,3-cyclohexanedione (2a–2e) and trifluoroacetophenones (1a–1d). The product formation was found to be dependent on various factors including pK_a of the 1,3-cyclohexanediones and gas-phase basicity of trifluoroacetophenones.

Graphical Abstract

Keywords:

• Aldol reaction
• β,β-disubstituted-13-cyclohexadiones
• diversity-oriented approach
• Michael addition

Acknowledgments

The authors would like to thank Syngenta Biosciences Pvt. Ltd. for supporting Mahesh K. and Damodar K. under the corporate PhD program and carrying out screening of the products under agrochemical screening module.