Microwave-assisted, solid-phase synthesis of a chiral 1,2,3,4-tetrahydro-quinoline library.
The synergy of a solution-phase preparation of scaffolds with a solid-phase combinatorial synthesis let to develop an efficient route to a small library of chiral, highly functionalized tetrahydroisoquinolines. Both loading on the Merrifield resin and the key acid-catalyzed Pictet-Spengler condensation were efficiently promoted by microwave irradiation. The library was designed such that up to five points of diversity would be potentially introduced, making the strategy in principle suitable for generation of a large number of compounds.
Lesma
Giordano
G
Dipartimento di Chimica Organica e Industriale e Centro Interdisciplinare Studi biomolecolari e applicazioni Industriali (CISI), Università degli Studi di Milano, via G. Venezian 21, 20133 Milan, Italy.
Danieli
Bruno
B
Lodroni
Francesco
F
Passarella
Daniele
D
Sacchetti
Alessandro
A
Silvani
Alessandra
A
D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008872:Microwaves; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011804:Quinolines