Title : Alpha-nitro ketone as an electrophile and nucleophile: synthesis of 3-substituted 2-nitromethylenetetrahydrothiophene and -tetrahydrofuran as drosophila nicotinic receptor probes - Zhang_2004_J.Org.Chem_69_876 |
Author(s) : Zhang N , Tomizawa M , Casida JE |
Ref : J Org Chem , 69 :876 , 2004 |
Abstract :
3-(6-Chloropyridin-3-yl)methyl-2-nitromethylenetetrahydrothiophene 2 and -tetrahydrofuran 3 were synthesized through novel approaches using alpha-nitro ketone intermediates as an electrophile and nucleophile, respectively. The 2-nitromethylenetetrahydrothiophene 2 was formed exclusively as the Z-isomer through intramolecular attack by a thiol substituent at the carbonyl group of an alpha-nitro ketone, in which the alpha-nitro ketone served as an electrophile. In contrast, the corresponding 2-nitromethylenetetrahydrofuran 3, not accessible by the above route due to limited stability, was prepared as a mixture of E- and Z-isomers by intramolecular attack of the alpha-nitro ketone enol anion in which the deprotonated alpha-nitro ketone served as a nucleophile. These compounds, together with the corresponding 2-nitromethylenepyrrolidine (1), were used to probe the Drosophila neonicotinoid-nicotinic acetylcholine receptor interaction. |
PubMedSearch : Zhang_2004_J.Org.Chem_69_876 |
PubMedID: 14750817 |
Zhang N, Tomizawa M, Casida JE (2004)
Alpha-nitro ketone as an electrophile and nucleophile: synthesis of 3-substituted 2-nitromethylenetetrahydrothiophene and -tetrahydrofuran as drosophila nicotinic receptor probes
J Org Chem
69 :876
Zhang N, Tomizawa M, Casida JE (2004)
J Org Chem
69 :876