Choline hydroxide, an efficient, green, and recyclable base catalyst, promoted the synthesis of 3-aroylflavones via Baker–Venkataraman rearrangement

ABSTRACT

3-Aroylflavones, a new synthesized group of flavones, have been recently studied via Baker–Venkataraman rearrangement under ‘one-pot’ or sequential ‘one-pot’ reaction conditions. Choline hydroxide, an inexpensive, easily prepared, and green homogeneous catalyst has been found to be the most efficient catalyst among several base catalysts such as KOH/pyridine, KOH/triethylamine, and CaO-ES/triethylamine in the sequential ‘one-pot’ synthesis of 3-aroylflavones. Moreover, the catalyst’s efficiency, and high recyclability to six times without considerable loss of 3-aroylflavones have enhanced the importance of the procedure. Furthermore, 1D-NMR, 2D-NMR, and HRMS have also been used to elucidate the structures of synthesized compounds.

GRAPHICAL ABSTRACT

KEYWORDS:

• 3-aroylflavone
• chromen-4-one
• choline hydroxide
• sequential one-pot synthesis
• Baker–Venkataraman rearrangement

Acknowledgements

All authors are grateful for all the support from Gam Thi Hong Ho, Cong-Danh Pham, Minh-Thu Thi Nguyen, Cong-Thang Duong, Vy Quynh Mong Le, Khang Nguyen, Ha Nguyen Phuong Tran, Khang Gia Tran, Tuyen Thi Ngoc Pham (University of Science, VNU-HCMC, Vietnam) and Prof. Dr. Poul Erik Hansen (University of Roskilde, Denmark).

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This research is funded by Vietnam National University, Ho Chi Minh City (VNU-HCM ) [grant number 562-2024-18-06].