Suzuki reaction on pyridinium N-haloheteroarylaminides: regioselective synthesis of 3,5-disubstituted 2-aminopyrazines
Authors
Castillo Romero, Rafael; Reyes Prados, María José; Izquierdo Ceinos, Ma Luisa; Álvarez-Builla Gómez, JulioIdentifiers
Permanent link (URI): http://hdl.handle.net/10017/2690DOI: 10.1016/j.tet.2007.11.057
ISSN: 0040-4020
Publisher
Elsevier
Date
2008Funders
The authors wish to thank the Comisión Interministerial de Ciencia y Tecnología (CICYT-BQU2001-1508 and CTQ2005-08902) and the Universidad de Alcalá (UAH GC2005/006) for financial support and the Ministerio de Educación y Ciencia (MEC) for two studentships (M.J.R. and R.C.). We also thank Professor Mijail Galajov for his assistance in the NMR study.
Comisión Interministerial de Ciencia y Tecnología
Universidad de Alcalá
Ministerio de Educación y Ciencia
Bibliographic citation
Tetrahedron, 2008, v. 64, n. 7, p. 1351-1370
Keywords
Cross-coupling reactions
Rapid analog syntheses
Heteroaromatic-compounds
Radical cyclization
Derivatives
Miyaura
Aminides
N-(2'-azinyl)aminides
N-2'-pyridylaminide
Heteroarylaminides
Chemistry, Organic
Project
info:eu-repo/grantAgreement/CICYT//BQU2001-1508/ESQUIMIODIVERSIDAD: NUEVOS MÉTODOS DE SÍNTESIS EN PARALELO PARA LA OBTENCIÓN DE MUESTROTECAS PRODUCTOS DE INTERÉS BIOLÓGICO
info:eu-repo/grantAgreement/CICYT//CTQ2005-08902/ES/N-AMIDAS DE AZINIO ESTABILIZADAS POR HETEROARILO: REACCIONES A TRAVÉS DE ORGANOPALADIOS, SÍNTESIS DE POLIAMINAS DENDRÍMERAS Y REACCIONES RADICALARIAS
info:eu-repo/grantAgreement/MEC//UAH GC2005%2F006/ES/N-AMINIDAS DE AZINIO ESTABILIZADAS POR HETEROARILO: REACCIONES A TRAVES DE ORGANOPALADIOS, SINTESIS DE POLIAMINAS DENDRÍMERAS Y REACCIONES RADICALARIAS
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Publisher's version
http://dx.doi.org/10.1016/j.tet.2007.11.057Rights
(c) Elsevier, 2008
Access rights
info:eu-repo/semantics/openAccess
Abstract
An extensive study of Suzuki–Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides has been performed. Mono- and disubstitution on 5- and 3,5-bromo derivatives produced the corresponding aryl derivatives. In the disubstituted compounds regioselective substitution at the 3-position occurred, vicinal to the aminide nitrogen, and this was more evident in pyrazine derivatives. The commonly used strategy involving N-alkylation and reduction of the N–N bond gave rise to a series of 2-alkylamino-3,5-disubstituted-pyrazines.
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