Synthesis of a boron-containing amidoxime reagent and its application to synthesize functionalized oxadiazole and quinazolinone derivatives

[Display omitted] Herein, we report the design, synthesis and application of a borylated amidoxime reagent for the direct synthesis of functionalized oxadiazole and quinazolinone derivatives. This reagent exhibits broad synthetic utility to obtain a variety of biologically relevant drug-like molecul...

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Bibliographic Details
Published in:Tetrahedron letters 2022-03, Vol.92, p.153657, Article 153657
Main Authors: Das, Bhaskar C., Nandwana, Nitesh K., P.Ojha, Devi, Das, Sasmita, Evans, Todd
Format: Article
Language:English
Subjects:
Boron based Therapeutics
Boron containing amidoxime
Imidazo[1,2-a]pyridine
Oxadiazoles
Quinazolinone
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Summary:[Display omitted] Herein, we report the design, synthesis and application of a borylated amidoxime reagent for the direct synthesis of functionalized oxadiazole and quinazolinone derivatives. This reagent exhibits broad synthetic utility to obtain a variety of biologically relevant drug-like molecules. It can be easily prepared at large scale from relatively inexpensive reagents, and can undergo facile transformations to obtain target compounds. The developed amidoxime reagent was synthesized from 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile and hydroxyl amine hydrochloride using N,N-diisopropylethylamine as a base in ethanol under reflux conditions. Overall advantages include a metal-free route to boronated oxadiazoles, quinazolinone derivatives, and restriction of the multistep sequences. Importantly, the boron-rich pharmacophore derived compounds were obtained through an efficient and inexpensive strategy.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.153657