Title: | Traceless synthesis of diketopiperazine fused tetrahydro-beta-carbolines on soluble polymer support |
Authors: | Chanda, Kaushik Chou, Cheng-Ting Lai, Jin-Ji Lin, Shu-Fen Yellol, Gorakh S. Sun, Chung-Ming 應用化學系 Department of Applied Chemistry |
Keywords: | Pictet-Spengler reaction;Soluble polymer-supported synthesis;Polyethylene glycol;Diketopiperazine;Tetrahydro-beta-carbolines |
Issue Date: | 1-May-2011 |
Abstract: | The Pictet-Spengler reaction, using polyethylene glycol immobilized tryptophan ester with a variety of ketones, was achieved by refluxing condition in acidic chloroform. The linear as well as cyclic ketones were employed. All the ketones were reacted within 6-8 h to furnish soluble polymer-supported tetrahydro-beta-carboline in good yields. Further expansion at N-terminus of tetrahydro-beta-carbolines was achieved through a reaction with chloroacetyl chloride. Finally, the 2,5-diketopiperazine skeleton was constructed over a beta-carboline by amination of the resulting N-chloroacetamides and subsequent intramolecular cyclization leading to cleavage of the polymer; constitutes a traceless synthesis of tetracyclic molecular architecture. Significantly, this strategy affords a straightforward and efficient approach for the construction of biological promising molecules with high purity and good yields. |
URI: | http://dx.doi.org/10.1007/s11030-010-9284-z http://hdl.handle.net/11536/8953 |
ISSN: | 1381-1991 |
DOI: | 10.1007/s11030-010-9284-z |
Journal: | MOLECULAR DIVERSITY |
Volume: | 15 |
Issue: | 2 |
Begin Page: | 569 |
End Page: | 581 |
Appears in Collections: | Articles |
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