Metal‐Catalyzed Cross‐Coupling Reactions of Aminopyridines

Abstract

The aminopyridines are key building blocks in the synthesis of bioactive heterocyclic compounds such as azaindoles and imidazopyridines. The role of metal-catalyzed methods in aminopyridine functionalization, in particular the catalytic systems used, reaction conditions and the influence of aminopyridine substituents on the reaction outcome, is outlined. The review covers different metal-catalyzed reactions developed for C-C and C-N bond formation. One-pot and multicomponent reactions directed towards aminopyridine-

Pd-Catalyzed Functionalization of Aryl Amines on a Soluble Polymer Support

“…Our group has been studying anilines and aminopyridines as suitable substrates on Pd-catalyzed functionalization reactions as well as on the synthesis of heterocycles such as indole and azaindole. 20,[25][26][27][28] Thus, we next tested the substrates immobilized on PEG-2000 (2b and 2e) under the Sonogashira reaction conditions. We first attempted the indolization reaction on PEG-2000, by testing 3b as starting material in the one-pot Sonogashira-cyclization reaction, which would hopefully lead to a PEG-supported 1,2-disubstituted indole.…”

Investigação de Aminopiridinas Não Halogenadas como Substratos Promissores para a Síntese de Azaindoles

“…O prémio Nobel da Química de 2010, atribuído a Negishi, Heck e Suzuki, contribuiu para o fortalecimento da importância da formação direta de ligações carbono-carbono através de métodos envolvendo catálise metálica [18]. Estes métodos têm vindo a transformar os procedimentos utilizados para construção e funcionalização de uma enorme variedade de compostos importantes [3].…”

“…Os azaindoles são bioisósteros do indole, e igualmente considerados como estruturas privilegiadas, que têm atraído o interesse da comunidade científica devido às suas propriedades farmacológicas, estando cada vez mais presentes em estruturas com interesse medicinal, como é o exemplo do inibidor da NAMPT (Esquema 1) [3].…”

Diels–Alder and Formal Diels–Alder Cycloaddition Reactions of Ynamines and Ynamides

“…In addition to the reactivity challenge associated with the unprecedented use of ynamides in inverse‐electron‐demand Diels–Alder cycloadditions, the final cycloadducts obtained are also valuable aminopyridines. These privileged scaffolds have found numerous applications in pharmaceutical science and agrochemistry …”