Current developments in the synthesis of 4-chromanone-derived compounds

Abstract

The chroman-4-one framework is a significant structural entity that belongs to the class of oxygen-containing heterocycles.

Visible‐Light‐Promoted Metal‐Free Photocatalytic Direct Aromatic C−H Oxygenation

“…4-chromanones are very important class of compounds due to their high prevalence in natural product and bioactive compounds. [17] We have synthesized several such chromanone/ chromane in good yield starting from corresponding 3-phenylpropan-1-ols and 2-phenylethan-1-ol in single step using this methodology (Table 4. 31-38).…”

Metal-Free Synthesis of Carbamoylated Chroman-4-Ones via Cascade Radical Annulation of 2-(Allyloxy)arylaldehydes with Oxamic Acids

“…Chroman-4-one is one of the most important structural motifs that occur in pharmaceuticals and natural products that exhibit various biological activities, such as antibacterial, antioxidant, SIRT2 inhibitors, anti-HIV and estrogenic properties [ 1 , 2 , 3 , 4 ]. In the past few years, great efforts have been devoted to access such compounds [ 5 , 6 ]. For example, the base-promoted condensation of 2-hydroxyacetophenones with aldehydes, the N -heterocyclic carbine (NHC)-catalyzed intramolecular Stetter reaction, and the 1,4-conjugate addition to chromones with various nucleophiles are among the representative methods [ 7 , 8 , 9 , 10 , 11 , 12 , 13 ].…”

Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation

“…Chroman-4-one scaffolds, a class of important oxygen-containing structural motifs, are ubiquitous in a plethora of natural products, drug candidates, and biologically active molecules ( Albrecht et al, 2005 ; Nibbs and Scheidt, 2011 ; Friden-Saxin et al, 2012 ; Lee et al, 2014 ; Seifert et al, 2014 ; Emami and Ghanbarimasir, 2015 ; Kumar et al, 2017 ; Mayuri et al, 2017 ). In the past years, the radical-initiated cascade cyclization strategy has attracted great attention for the construction of chroman-4-one scaffold and other (hetero)cyclic frameworks ( Zhao et al, 2016 ; Yang et al, 2017 ; Hu et al, 2018a ; Hu et al, 2018b ; Liu et al, 2019 ; Sheng et al, 2019 ; Xiao et al, 2019 ; Zhou et al, 2019a ; Das et al, 2020 ; Han et al, 2020 ; Huang et al, 2020 ; Liu et al, 2020 ; Mei et al, 2020 ; Xiong et al, 2020 ; Diana et al, 2021 ). Particularly, the photocatalytic radical-initiated cascade cyclization, including two mechanistically distinctive pathways, has emerged as an elegant, green, and powerful strategy for the synthesis of such scaffold and its derivatives.…”