Microwave-assisted synthesis of tetracyclic 2,5-diketopiperazines on a soluble polymer support: A structural analogue of tadalafil

Wong Jin Chang, Kaushik Chanda, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Structural analogues of tadalafil that contain two diversity points have been synthesized from a soluble polymer support employing a PictetSpengler reaction using focussed microwave irradiation. Polymer-bound deprotected tryptophan reacts with various aldehydes to generate the tetrahydro - carbolines on the support. Subsequently immobilized tetrahydro - carboline underwent a highly efficient intramolecular N-heterocyclization in a traceless fashion from various in-situ generated -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.

Original languageEnglish
Pages (from-to)42-50
Number of pages9
JournalAustralian Journal of Chemistry
Volume62
Issue number1
DOIs
StatePublished - 4 Feb 2009

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