Abstract
In this work, we report a practical method for alkylation of saturated heterocycles with chloroacetone yielding prochiral heterocyclic ketones, including previously not described molecules. The desired building blocks were obtained with high yields in hydrochloric salt forms, without the need for chromatographic purification.
Highlights
In this work, we report a practical method for alkylation of saturated heterocycles with chloroacetone yielding prochiral heterocyclic ketones, including previously not described molecules
Prochiral aminoketones bearing different saturated heterocycles represent an important group of building blocks that can be utilized for the synthesis of active pharmaceutical ingredients containing polyamines (such as selective P2X3 receptor antagonist RO-85 for inflammatory pain (1) [1], potential anticancer agent LPA2 (EDG4) antagonists [2], anti-inflammatory Cancer Osaka thyroid (COT) kinase inhibitors [3], potential antimalarial 4-aminoquinoline derivatives [4]), amino alcohols (such as analgesic 5-HT receptor agonists (2) [5]) and oximes (Fig. 1)
A variety of reactions can be employed for the synthesis of the saturated heterocyclic aminoketones (Fig. 2), such as Grignard-type substitution (I) [7], intermolecular α-carbonyl carbene insertion (II) [8], alkylation with chloroacetone (III) [9], Rabe amination (IV) [10], alcohol amination (V) [11] and multicomponent alkylation (VI) [12]
Summary
A variety of reactions can be employed for the synthesis of the saturated heterocyclic aminoketones (Fig. 2), such as Grignard-type substitution (I) [7], intermolecular α-carbonyl carbene insertion (II) [8], alkylation with chloroacetone (III) [9], Rabe amination (IV) [10], alcohol amination (V) [11] and multicomponent alkylation (VI) [12]. We describe a rapid and catalyst-free method for the synthesis of different aminoketones starting from the respective saturated heterocycles
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