Solid-phase synthesis of imidazoquinazolinone derivatives with three-point diversity

A novel imidazoquinazolinone-based tricyclic structure with three-point diversity has been synthesized using solid-phase methodology. The compounds were obtained by treating the amino group of polymer-linked amino acids with 2-nitrobenzaldehyde followed by reduction of the nitro group to an amine. D...

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Bibliographic Details
Published in:Tetrahedron 2005-01, Vol.61 (3), p.629-635
Main Authors: Kesarwani, Amit P., Grover, Rajesh K., Roy, Raja, Kundu, Bijoy
Format: Article
Language:English
Subjects:
Imidazoquinazolinone
Isothiocyanates
Solid-phase methodology
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Summary:A novel imidazoquinazolinone-based tricyclic structure with three-point diversity has been synthesized using solid-phase methodology. The compounds were obtained by treating the amino group of polymer-linked amino acids with 2-nitrobenzaldehyde followed by reduction of the nitro group to an amine. Derivatization of amine with isothiocyanates and cyclization of the resulting thioureas with DIC followed by acidolytic cleavage yielded the desired imidazoquinazolinone based compounds in high purity and moderate to high yield. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.10.090