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Issue 31, 2017
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An aryne-based three-component access to α-aroylamino amides

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Abstract

Aryne chemistry has recently received widespread attention and isocyanides have been reported as efficient nucleophilic partners in a set of multicomponent transformations. In this study, we demonstrate that tertiary α-monosubstituted α-isocyanoacetamides are efficaciously coupled with water and benzyne to offer a direct and metal-free access to densely functionalized α-benzoylamino amides, without competing with the intramolecular cyclization to 5-aminooxazoles. Despite the formation of the aryl anion as a key intermediate, the reaction displays a stereoconservative course, allowing for the preparation of enantiomerically pure α-benzoylamino amides. Finally, the synthetic utility of the reported MCR was exemplified by the preparation of proglumide, a cholecystokinin antagonist.

Graphical abstract: An aryne-based three-component access to α-aroylamino amides

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Publication details

The article was received on 12 Jul 2017, accepted on 18 Jul 2017 and first published on 19 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01715D
Citation: Org. Biomol. Chem., 2017,15, 6604-6612
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    An aryne-based three-component access to α-aroylamino amides

    M. Serafini, A. Griglio, S. Viarengo, S. Aprile and T. Pirali, Org. Biomol. Chem., 2017, 15, 6604
    DOI: 10.1039/C7OB01715D

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