Abstract
An efficient synthetic route has been described for the alkylation of 1$H$-indole, 1$H$-benzimidazole, and 1$H$-benzotriazole. This approach features the alkylation of heteroaromatics through in situ generated enones from ketonic Mannich bases under metal-free conditions. A series of alkylated heteroaromatics have been synthesized via the K10 catalyzed alkylation reactions of these heteroaromatics with a variety of ketonic Mannich bases. Environmentally benign K10 catalyst, water-mediated mild reaction conditions, and the efficient synthesis of alkylated products are the advantages of this alkylation method.
Highlights
Indole, benzimidazole, and benzotriazole derivatives appear in a wide range of biologically active compounds on both the synthetic and the natural basis
Alkyl functionalized indole, benzimidazole, and benzotriazole derivatives show such bioactivities. 8−10 Given the importance of these functionalized heteroaromatics in medicinal chemistry, development of an environmentally friendly synthetic route to these heteroaromatics is of high importance
Various synthetic methods have been applied to the alkylation of these heteroaromatics; very limited studies have been reported on the synthesis of carbonyl functionality bearing alkyl substituted indoles, benzimidazoles, and benzotriazoles
Summary
Benzimidazole, and benzotriazole derivatives appear in a wide range of biologically active compounds on both the synthetic and the natural basis These heteroaromatics exhibit biological activities such as antiparasitic, 1 antimicrobial, 2 antiviral, 3 antiserotonergic, antiadrenergic, antihistaminic, and analgesic. It is aimed to achieve the metal-free alkylation of 1 H -indole, 1 H -benzimidazole, and 1 H -benzotriazole from the reaction of these heteroaromatics with Mannich bases in water. In this approach, Mannich base 1 serves as an enone precursor for 2 as given in Scheme 1.
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