Aminocarbonylation of 4-Iodo-1H-imidazoles with an Amino Acid Amide Nucleophile: Synthesis of Constrained H-Phe-Phe-NH2 Analogues

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• 作者：Anna Skogh ; Rebecca Fransson ; Christian Sk枚ld ; Mats Larhed ; Anja Sandstr枚m
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：December 6, 2013
• 年：2013
• 卷：78
• 期：23
• 页码：12251-12256
• 全文大小：314K
• 年卷期：v.78,no.23(December 6, 2013)
• ISSN：1520-6904

文摘

A simple and an expedient process to prepare 5-aryl-1-benzyl-1H-imidazole-4-carboxamides by the aminocarbonylation of 5-aryl-4-iodo-1H-imidazoles using ex situ generation of CO from Mo(CO)₆ with an amino acid amide nucleophile is reported. Furthermore, a microwave-assisted protocol for the direct C-5 arylation of 1-benzyl-1H-imidazole and a regioselective C-4 iodination method to acquire starting material for our aminocarbonylation are presented. The method can be used to prepare imidazole based peptidomimetics, herein exemplified by the synthesis of constrained H-Phe-Phe-NH₂ analogues.