Pyridinium N-2´-pyridylaminide: synthesis of 3-aryl-2-aminopyridines through an intramolecular radical process

Authors
Sánchez Muñoz, AránzazuUniversity of Alcalá Author; Núñez Ventura, AraceliUniversity of Alcalá Author; Álvarez-Builla Gómez, JulioUniversity of Alcalá Author; Burgos García, CarolinaUniversity of Alcalá Author
Identifiers
Permanent link (URI): http://hdl.handle.net/10017/4190
DOI: 10.1016/j.tet.2004.09.099
ISSN: 0040-4020
Publisher
Elsevier
Date
2004
Affiliation
Universidad de Alcalá. Departamento de Química Orgánica
Funders
Financial support by the Comisión Interministerial de Ciencia y Tecnología (CICYT, project BQU2001-1508) and two grants, by the Universidad de Alcalá (A. S.) and by Ministerio de Educación y Ciencia (Spain) (A. N.) are gratefully acknowledged.
Bibliographic citation
Tetrahedron, 2004, v. 60, n. 51, p. 11843-11850
Keywords
Arylation
Biaryls
Ipso-substitution mechanism
Radicals and radical reaction
Tris(trimethylsilyl)silane
Project
BQU2001-1508 (Comisión Interministerial de Ciencia y Tecnología-CICYT)
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Publisher's version
http://dx.doi.org/10.1016/j.tet.2004.09.099
Rights
(c) Elsevier, 2004
Access rights
info:eu-repo/semantics/openAccess
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Abstract
Tris(trimethylsilyl)silane (TTMSS) and azobisisobutironitrile (AIBN) promote the intramolecular heteroarylation of arenesulfonamides with pyridyl radicals under thermal conditions. The arenesulfonamides are easily prepared from pyridinium N-2′-pyridylaminide. The heteroarylation process involves pyridyl radical cyclization and ipso substitution.
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