Development of a practical solid-phase synthesis approach to 1,3,5-triazepan-2,6-diones

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• 作者：Joel Boeglin ; Claire Venin ; Gilles Guichard
• 关键词：Peptidomimetics ; Heterocycles ; Ureas ; Peptides ; Solid phase synthesis
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：9 September, 2012
• 年：2012
• 卷：68
• 期：36
• 页码：7472-7478
• 全文大小：571 K

文摘

1,3,5-Triazepan-2,6-diones are a class of conformationally restricted heterocycles derived from dipeptides. With the aim to develop a general and practical method useful for library production, three polymer-assisted syntheses, all based on a catch and release approach, have been evaluated and compared. The method involving a Hofmann rearrangement of N-Boc dipeptide carboxamides and subsequent trapping of the isocyanate on polymer-supported N-hydroxysuccinimide (PS-HOSu) was found to be the most reliable and versatile, allowing rapid access to the 1,3,5-triazepan-2,6-dione skeleton.