Functionalization of Hydroanthraquionones Using Diel-Alders Approach

Functionalization of Hydroanthraquionones Using Diel-Alders Approach
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Abstract
Diel-Alder (DA) reaction involves the reaction of a diene with a mono-ene resulting in the formation of cyclohexene derivative. The DA reaction plays a central in the construction of organic intermediates with the advantage of having a total atom efficiency with no by-products. One of the most common DA processes is [4+2] cycloaddition that is vastly applied in industries to manufacture complex organic derivatives. . In this study, a reliable and efficient synthetic procedure for developing diverse hydro anthraquinones is proposed. The study suggests the use of the Diels-Alder reaction in building hydro anthraquinones from its simple precursors. The study uses a two-step route technique. The process involves using dimethoxy naphthalene to synthesize highly activated dienophiles that can be utilized in [4+2] cycloaddition. The reaction is conducted using standard Schlenk Techniques under argon atmosphere by using flame-dried glassware. The study established that The DA reactions enabled the direct access of highly functionalized derivatives anthraquinone. The process involved the substitution of 2-substituted 14-naphthoquinone with other dienes in cycloaddition.
Key Words: Diel-Alder reaction, cycloaddition, hydro anthraquinones
Functionalization of Hydroanthraquionones Using Diel-Alders Approach
Fungi produce secondary metabolites with a substantial content of anthraquinone compounds. The anthraquinone compounds have a vast range of physiological activities, such as antimicrobial and anti-cancer properties. Further, the compounds exhibit chromatic elements that can be used in the manufacturing of dyes. Indeed, hydro anthraquinones have been reported to have cytotoxic and anti-bacterial properties. Some mycotoxins, such as beticolins, are natural sources of hydro anthraquinones moieties. Usually, the moieties are connected to a chlorinated tetra-hydroxanthone through a nonane ring system called bicyclo [3.2.2] ring (Wilborn et al., 2019). The natural compound has various physiological properties, such as antiproliferative effects on carcinogenic properties due to their ability to form ion channels. However, limited studies have been conducted on the synthetic approaches of hydro anthraquinones products. In this study, a reliable and efficient synthetic procedure for developing diverse hydro anthraquinones is proposed. The study suggests the use of the Diels-Alder reaction in building hydro anthraquinones from its simple precursors.
Background
Diel-Alder (DA) reaction involves the reaction of a diene with a mono-ene resulting in the formation of cyclohexene derivative. The DA reaction plays a central in the construction of organic intermediates with the advantage of having a total atom efficiency with no by-products (Hammoudan, 2020). One of the most common DA processes is [4+2] cycloaddition that is vastly applied in industries to manufacture complex organic derivatives. Dienophiles such as Quinones were the first examples examined by Diels and Alder (Farshchi et al., 2021). They are highly reactive and synthetically useful materials in pericyclic reactions. Thus, they are helpful dienophi...