Title: Microwave-Assisted Synthesis of Tetracyclic 2,5-Diketopiperazines on a Soluble Polymer Support: A Structural Analogue of Tadalafil
Authors: Chang, Wong-Jin
Chanda, Kaushik
Sun, Chung-Ming
Department of Applied Chemistry
Issue Date: 2009
Abstract: Structural analogues of tadalafil that contain two diversity points have been synthesized from a soluble polymer support employing a Pictet-Spengler reaction using focussed microwave irradiation. Polymer-bound deprotected tryptophan reacts with various aldehydes to generate the tetrahydro-beta-carbolines on the support. Subsequently immobilized tetrahydro-beta-carboline underwent a highly efficient intramolecular N-heterocyclization in a traceless fashion from various in-situ generated alpha-alkyl and heteroalkyl amides in two steps to generate tetracyclic 2,5-diketopiperazines in high purity. All the compounds were isolated as cis and trans isomers with good yields.
URI: http://hdl.handle.net/11536/7777
ISSN: 0004-9425
DOI: 10.1071/CH08334
Volume: 62
Issue: 1
Begin Page: 42
End Page: 50
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