Abstract
We describe the use of bismuth(III) triflate as an efficient and environmentally friendly catalyst for the Nazarov reaction of aryl vinyl ketones, leading to the synthesis of 3-aryl-2-ethoxycarbonyl-1-indanones and 3-aryl-1-indanones. By changing the temperature and reaction time, it was possible to modulate the reactivity, allowing the synthesis of two distinct product classes (3-aryl-2-ethoxycarbonyl-1-indanones and 3-aryl-1-indanones) in good to excellent yield. The reaction did not require additives and was insensitive to both air and moisture. Preliminary biological evaluation of some indanones showed a promising profile against some human cancer line cells.
Keywords:
Nazarov reaction; bismuth; catalysis; heterocycles; indanones.
Copyright © 2024, Rodrigues Jr. et al.
Grants and funding
The authors thank the São Paulo Foundation Science (FAPESP, #2018/02611-0, #2013/07600-3 and #2023/18007-3, to FC) for financial support. F. C. is also grateful to the Brazilian National Council for Scientific and Technological Development (CNPq) for financial support and a research fellowship (#306142/2022-8). This study was partly funded by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Brasil. H. S. (#2015/09205-0) thanks FAPESP for a Ph.D. fellowship. L. A. Z. thanks CNPq for his fellowship. This study was also supported by the grants #2017/24993-0, #2019/23864-7, and #2015/17177-6, São Paulo Research Foundation (FAPESP) and grants #402587/2016-2, #306142022-8, and #407960/2023-6, Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES).