Microwave-assisted traceless synthesis of hydantion-fused β-carboline scaffold

Wen Pin Yeh, Wong Jin Chang, Mei Lian Sun*, Chung-Ming Sun

*Corresponding author for this work

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

Multistep microwave-assisted reactions toward the synthesis of hydantoin-fused tricyclic tetrahydro-β-carbolines on the soluble polymer support have been developed. Polymer-bound tryptophan with various aldehydes has been subjected to Pictet-Spengler reaction to obtain tricyclic β-carboline conjugates. The terminal hydantoinyl moiety is constructed across polymer-bound β-carbolines by the reaction with various isocyanates under microwave irradiation to form urea intermediate. Simultaneous intramolecular cyclization of urea followed by cleavage of the polymer support leads to a traceless synthesis of tetracyclic scaffolds in high yield and high purity.

Original languageEnglish
Pages (from-to)11809-11816
Number of pages8
JournalTetrahedron
Volume63
Issue number48
DOIs
StatePublished - 26 Nov 2007

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