A concise synthesis of 10-benzoyl-3,4-dihydroanthracen-1(2H)-one derivatives catalyzed by TfOH under metal-free conditions

Abstract

TfOH was proved to be an efficient catalyst to promote the intra-molecular cyclization, Diels-Alder reaction, deprotonation and dehydration, and provided a concise synthesis of 10-benzoyl-3,4-dihydroanthracen-1(2H)-ones in good yields from a reaction of 2-(phenylethynyl) benzaldehyde and cyclohexane-1,3-dione. It underwent in high regioselectivity when center asymmetrical 4,4-dimethylcyclohexane-1,3-dione was used as a reactant.

Graphical Abstract

TfOH was proved to be an efficient catalyst to promote a reaction of 2-(phenylethynyl) benzaldehyde and cyclohexane-1,3-dione to provide a concise procedure for the synthesis of 10-benzoyl-3,4-dihydroanthracen-1(2H)-ones in good yields.

Keywords:

• Anthracene
• 2-(phenylethynyl)benzaldehyde
• regioselectivity
• TfOH

Additional information

Funding

This work was financially supported by NSFC of China [No. 21702078], Natural Science Foundation of Jiangsu Province [BK20181001], Natural Science Foundation of Jiangsu Higher Education Institution [17KJA150003] and TAPP, the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.