Development of a practical solid-phase synthesis approach to 1,3,5-triazepan-2,6-diones |
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Authors: | Joel Boeglin Claire Venin Gilles Guichard |
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Affiliation: | 1. Université de Bordeaux?CNRS UMR5248, Institut Européen de Chimie et Biologie, CBMN, 2 rue Robert Escarpit, Pessac 33607, France;2. CNRS, Institut de Biologie Moléculaire et Cellulaire, Laboratoire d’Immunologie et Chimie Thérapeutiques, Strasbourg 67000, France |
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Abstract: | 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. |
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