Application of Organolithium Compounds in Organic Synthesis. XIX. Synthetic Strategies Based on Aromatic Metallation. A Concise Regiospecific Synthesis of 3-Halogenated Picolinic and Isonicotinic Acids

Autor:	J. Epsztajn, A. Grabowska, M. W. Płtka
Rok vydání:	1997
Předmět:	chemistry.chemical_compound Hydrolysis Chemistry Organolithium compounds Organic Chemistry Organic chemistry Picoline Organic synthesis Isonicotinic acid
Zdroj:	Synthetic Communications. 27:1075-1086
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397919708003053
Popis:	The synthesis of the halogenated picolin- and isonicotinanilides (3) and (4) via metallation (n-BuLi) of the anilides (1) and (2) and then the reaction of the generated bis-lithiated anilides with halogenating agents (CCI3-CCI3, CH2Br-CH2Br, I2) followed by subsequent acidic hydrolysis of (3) and (4), as a way of regiospecific transformation of picoline and isonicotine acids into their C3-halogenated derivatives, is described.
Databáze:	OpenAIRE
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