Synthesis of some novel chloro-/aryl-substituted-5,5-dimethyl-2-cyclohexenones

Abstract

Two novel structural isomers: the dihalo-5,5-dimethyl-2-cyclohexenones were synthesized. Regioselective Suzuki-Miyaura cross coupling reaction of the isomers with nine different aryl boronic acids afforded eighteen novel compounds: the 2-aryl-3-chloro-5,5-dimethyl-2-cyclohexenones and the 3-aryl-2-chloro-5,5-dimethyl-2-cyclohexenones in 90–95% yields, which were characterized spectroscopically by IR, NMR and MS. The single crystal X-Ray diffraction ORTEP views of four representative compounds unambiguously confirm the formation of substituted cyclohexenones.

Graphical Abstract

Keywords:

• Aryl derivatives
• cross coupling reaction
• halogenated cyclohexenones
• single crystal XRD

Acknowledgments

The authors thank (1) JCAS for Council of Scientific and Industrial Research (CSIR), Govt. of India, New Delhi, INDIA; CSIR SRF – File no. 09/039(0119)/2018-EMR-1, dated April 16, 2018.; (2) Bengaluru Central University.; (3) Bangalore University and (4) Dr. B. S. Bandodkar, Pharmaron Chemical Company, Beijing, China for all help rendered; (5) Suman Bharadwaj, Christ University, Bangalore.; and (6) Avinash, R., Bangalore; Sreenatha, N. R., Hassan.

Additional information

Funding

The author JCAS is thankful to Council of Scientific and Industrial Research (CSIR), Govt. of India, New Delhi, INDIA; CSIR SRF – File no. 09/039(0119)/2018-EMR-1, dated April 16, 2018, for providing the financial support.