Application of organolithium compounds in organic synthesis. Part 19. Synthetic strategies based on aromatic metallation. A concise regiospecific synthesis of 3-halogenated picolinic and isonicotinic acids

Article abstract of DOI:10.1080/00397919708003053

The synthesis of the halogenated picolin- and isonicotinalides (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 (CCl₃-CCl₃, 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.

Full text of DOI:10.1080/00397919708003053

This article was downloaded by: [University of Hong Kong Libraries]
On: 27 July 2013, At: 02:27
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
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
J. Epsztajn a , M. W. Płtka a & A. Grabowska a
a Department of Organic Chemistry, University of
Łódź, 90-136, Lódź, Narutowicza 68, Poland
Published online: 22 Aug 2006.
To cite this article: J. Epsztajn , M. W. Ptka & A. Grabowska (1997) 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, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 27:6, 1075-1086
To link to this article: http://dx.doi.org/10.1080/00397919708003053
PLEASE SCROLL DOWN FOR ARTICLE

Taylor & Francis makes every effort to ensure the accuracy of all the
information (the “Content”) contained in the publications on our platform.
However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness,
or suitability for any purpose of the Content. Any opinions and views
expressed in this publication are the opinions and views of the authors, and
are not the views of or endorsed by Taylor & Francis. The accuracy of the
Content should not be relied upon and should be independently verified with
primary sources of information. Taylor and Francis shall not be liable for any
losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or
indirectly in connection with, in relation to or arising out of the use of the
Content.
This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden. Terms & Conditions of access and use can be found at
http://www.tandfonline.com/page/terms-and-conditions