A new efficient synthetic methodology for tetrahydroisoquinoline and tetrahydro-beta-carboline derivatives using the Pictet-Spengler reaction.
A new solution-phase methodology microwave-assisted for improving the Pictet-Spengler reaction in the synthesis of the tetrahydroisoquinoline and beta-carboline derivatives has been reported. This methodology was applied to obtain a small library of tetrahydroisoquinoline and beta-carboline derivatives using L-Dopa, dopamine, and tryptophan, as well as a variety of commercially available aldehydes as starting material. The use of such nonconventional reaction conditions reveals several features like a short reaction time compared to conventional eating, ease of isolation of the products after work-up, and improvement of the yields. This new one-pot protocol would be an ideal and rapid method to synthesize compounds in a combinatorial context.
Campiglia
Pietro
P
Dipartimento di Chimica Farmaceutica e Tossicologica, University of Naples "Federico II", Naples, Italy.
Gomez-Monterrey
Isabel
I
Lama
Teresa
T
Novellino
Ettore
E
Grieco
Paolo
P
D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D004298:Dopamine / Q000737:chemistry; D007980:Levodopa / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D008956:Models, Chemical; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013997:Time Factors; D014364:Tryptophan / Q000737:chemistry
D002243:Carbolines; D044005:Tetrahydroisoquinolines; D007980:Levodopa; C009804:tryptoline; D014364:Tryptophan; D004298:Dopamine