Multicomponent reactions with dihydroazines: efficient synthesis of a diverse set of pyrido-fused tetrahydroquinolines.
A multicomponent assembly of pyrido-fused tetrahydroquinolines is accomplished in a one-pot process from the interaction of dihydroazines, aldehydes, and anilines. A rational screening of the different components and parameters of this reaction, such as the range of reactive starting materials, catalysts and reaction conditions (solvent range; thermal, high pressure- and microwave-promoted processes) is carried out. Optimized conditions allow an efficient preparation of pyrido-fused tetrahydroquinolines with good yields, bypassing the biomimetic NADH-like reductive pathway which is typical in the interaction of dihydropyridines with carbonyl compounds and amines. Furthermore, solid-supported versions of the process have been developed, which should facilitate the preparation of libraries.
Carranco
Inés
I
Parc Científic de Barcelona, University of Barcelona, Josep Samitier 1-5, 08028 Barcelona, Spain.
Díaz
José Luis
JL
Jiménez
Oscar
O
Vendrell
Marc
M
Albericio
Fernando
F
Royo
Miriam
M
Lavilla
Rodolfo
R
D000447:Aldehydes / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*
D000447:Aldehydes; D000814:Aniline Compounds; D011728:Pyridones; D011804:Quinolines; D006859:Hydrogen; C023650:aniline