RT Journal Article
T1 Mechanochemical Aza-Vinylogous Povarov Reactions for the Synthesis of Highly Functionalized 1,2,3,4-Tetrahydroquinolines and 1,2,3,4-Tetrahydro-1,5-Naphthyridines
A1 Clerigué Louzado, José
A1 Ramos García, María Teresa
A1 Menéndez Ramos, José Carlos
AB The aza-vinylogous Povarov reaction between aromatic amines, α-ketoaldehydes or α-formylesters and α,β-unsaturated dimethylhydrazones was carried out in a sequential three-component fashion under mechanochemical conditions. Following extensive optimization work, the reaction was performed on a vibratory ball mill operating at 20 Hz and using zirconium oxide balls and milling jar, and afforded 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro- 1,5-naphthyridines functionalized at C-2, C-4 and also at C-6, in the latter case. This protocol generally afforded the target compounds in good to excellent yields and diastereoselectivities. A comparison of representative examples with the results obtained under conventional conditions revealed that the mechanochemical protocol affords faster Povarov reactions in comparable yields using a solvent-less environment.
PB MDPI
SN 1420-3049
YR 2021
FD 2021-03-02
LK https://hdl.handle.net/20.500.14352/7095
UL https://hdl.handle.net/20.500.14352/7095
LA eng
NO MICINN (grant RTI2018-097662-B-I00)
NO Universidad Complutense (predoctoral contract to JC)
DS Docta Complutense
RD 28 abr 2025