RT info:eu-repo/semantics/article
T1 Suzuki reaction on pyridinium N-haloheteroarylaminides: regioselective synthesis of 3,5-disubstituted 2-aminopyrazines
A1 Castillo Romero, Rafael
A1 Reyes Prados, María José
A1 Izquierdo Ceinos, Ma Luisa
A1 Álvarez-Builla Gómez, Julio
K1 Cross-coupling reactions
K1 Rapid analog syntheses
K1 Heteroaromatic-compounds
K1 Radical cyclization
K1 Derivatives
K1 Miyaura
K1 Aminides
K1 N-(2'-azinyl)aminides
K1 N-2'-pyridylaminide
K1 Heteroarylaminides
K1 Chemistry, Organic
K1 Bioquímica
K1 Biochemistry
K1 Science
K1 Ciencia
AB 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.
PB Elsevier
SN 0040-4020
YR 2008
FD 2008
LK http://hdl.handle.net/10017/2690
UL http://hdl.handle.net/10017/2690
LA eng
NO 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.
DS MINDS@UW
RD 20-abr-2024