Abstract
An electron-transfer chain reaction between 2-nitropropane anion and alpha-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-yl)ethanone or 2-bromo-1-(4-nitrophenyl)ethanone were reacted with several cyclic nitronate anions to form alpha,beta-unsaturated ketones via a S(RN)1 mechanism. This new method can be used to synthesize a wide variety of chalcone analogues.
Highlights
Introduction α,β-Unsaturated ketones are useful key intermediates [1,2] bearing the well-known chalcone pharmacophore
The synthesis of such structures from α-bromocarbonyl compounds was developed with the SRN1 methodology
Such an electron-tranfer chain reaction between 2-nitropropane anion and halomethyl substrates led to a mixture of a C-alkylation product and an ethylenic compound resulting from nitrous acid elimination from the former alkylation product [8,9,10]
Summary
Introduction α,β-Unsaturated ketones are useful key intermediates [1,2] bearing the well-known chalcone pharmacophore. We have established a convenient synthesis of α,β-unsaturated ketones 5 and 6 by the reaction of α-bromoketones derived from 5-nitrothiophene and 4-nitrobenzene with nitropropyl anion 4.
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