Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality.
[Structure: see text] In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation.
Paravidino
Monica
M
Vrije Universiteit Amsterdam, Department of Chemistry, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.
Bon
Robin S
RS
Scheffelaar
Rachel
R
Vugts
Danielle J
DJ
Znabet
Anass
A
Schmitz
Rob F
RF
de Kanter
Frans J J
FJ
Lutz
Martin
M
Spek
Anthony L
AL
Groen
Marinus B
MB
Orru
Romano V A
RV