Suzuki reaction on pyridinium N-haloheteroarylaminides: regioselective synthesis of 3,5-disubstituted 2-aminopyrazines
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 oc...
| Autores: | , , , |
|---|---|
| Tipo de documento: | artigo |
| Data de publicação: | 2008 |
| País: | España |
| Recursos: | Universidad de Alcalá (UAH) |
| Repositório: | e_Buah Biblioteca Digital Universidad de Alcalá |
| Idioma: | inglês |
| OAI Identifier: | oai:ebuah.uah.es:10017/2690 |
| Acesso em linha: | http://hdl.handle.net/10017/2690 https://dx.doi.org/10.1016/j.tet.2007.11.057 |
| Access Level: | Acceso aberto |
| Palavra-chave: | Cross-coupling reactions Rapid analog syntheses Heteroaromatic-compounds Radical cyclization Derivatives Miyaura Aminides N-(2'-azinyl)aminides N-2'-pyridylaminide Heteroarylaminides Chemistry, Organic Bioquímica Ciencia Biochemistry Science |
| Resumo: | 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. |
|---|