79965-62-1Relevant articles and documents
Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution
Antoniak, Damian,Barbasiewicz, Micha?
supporting information, p. 516 - 519 (2022/01/20)
Electrophilic nitropyridines react with sulfonyl-stabilized carbanions to give products of C-H alkylation via vicarious nucleophilic substitution. The process consists of formation of the Meisenheimer-type adduct followed by base-induced β-elimination of the sulfinic acid (e.g., PhSO2H). Mechanistic studies reveal that in the latter step alkyl substituent and adjacent nitro group tend to planarize for effective stabilization of benzyl anion, and thus, adduct of hindered isopropyl carbanion remains stable toward elimination for steric reasons.
Naphthyridines. IV. Synthesis of Benzo-1,7-naphthyridines
Baumgarten, Henry E.,Barkley, Raymond P.,Chiu, Shuet-Hing Lee,Thompson, Robert D.
, p. 925 - 928 (2007/10/02)
Benzo-1,7-naphthyridines have been synthesized from 3-nitrolepidine (3) by a sequence involving monobromination of the methyl group of 3, oxidation of the bromomethyl group to the carboxyaldehyde group by Franzen's trimethylamine N-oxide procedure, and
