The reaction of nucleophilic reagents at the .BETA.-position of 3-bromo-4-nitropyridine N-oxides.

DOI DOI DOI DOI PDF View 1 Remaining Hide 2 Citations 7 References Open Access

Bibliographic Information

Other Title
  • The Reaction of Nucleophilic Reagents at the β-Position of 3-Bromo-4-nitropyridine <i>N</i>-Oxides
  • The Reaction of Nucleophilic Reagents at the β-Position of 3-Bromo-4-nitropyridine <i>N</i>-Oxide
  • ChemInform Abstract: THE REACTION OF NUCLEOPHILIC REAGENTS AT THE BETA‐POSITION OF 3‐BROMO‐4‐NITROPYRIDINE‐N‐OXIDE

Search this article

Description

The reactions of 3-bromo-4-nitro-2-R1-6-R2-5-X-pyridine N-oxides (1a:R1=H, R2=Me, X=H; 1b:R1=R2=Me, X=H; 1c: R1=R2=H, X=Br) with diethyl sodiomalonate, ethyl sodiocyanoacetate, and ethyl sodioacetoacetate have been carried out. The treatment of 1a, 1b, and 1c with diethyl sodiomalonate gives 3-[bis(ethoxycarbonyl)methyl]-4-nitro-2-R1-6-R2-5-X-pyridine N-oxides (2a, 2b, and 2c) and 4-[bis(ethoxycarbonyl)methyl]-3,5-dibromopyridine N-oxides (3c). With ethyl sodiocyanoacetate, 3-[cyano(ethoxycarbonyl)methyl]-4-nitro-2-R1-6-R2-pyridine N-oxides (4a and 4b) and 4-[cyano(ethoxycarbonyl)methyl]-3,5-dibromopyridine N-oxide (5c) are obtained. With ethyl sodioacetoacetate, 1a and 1c give 3-[acetyl(ethoxycarbonyl)methyl]-6-methyl-4-nitropyridine N-oxide (6a) and/or 3-ethoxycarbonyl-2-methyl-6-R1-7-X-furo[3,2-c]pyridine N-oxides (7a and 7c), but 1b is unaffected by ethyl sodioacetoacetate under the given conditions. The electronic and steric effects of methyl and bromo groups for the reactions are discussed.

Journal

Citations (2)*help

See more

References(7)*help

See more

Keywords

Details 詳細情報について

Report a problem

Back to top