Access to newly functionalized imidazole derivatives: efficient synthesis of novel 5-amino-2-thioimidazoles using propylphosphonic anhydride (®T3P)

doi:10.1016/j.tetlet.2015.01.046

Tetrahedron Letters

Volume 56, Issue 8, 18 February 2015, Pages 1011-1014

https://doi.org/10.1016/j.tetlet.2015.01.046 Get rights and content

Abstract

We describe here an efficient method to synthesize 5-amino-2-thioimidazole compounds by T3P-mediated cyclization of N-acetamidoisothiourea intermediates. The newly functionalized 5-amino-2-thioimidazole compounds are finally obtained in 5 steps from an amine as starting block.

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Acknowledgments

We are grateful to the institutions that support our laboratory: INSERM, Université de Lille, Institut Pasteur de Lille. This project was supported by Conseil Régional Nord-Pas de Calais, EDFR (convention 11003609), Etat DRRT, PRIM and Université Lille 2 (Appel à projets «orientations stratégiques»: convention A007). Manuel Lasalle is a recipient of a doctoral fellowship of the French Ministere de la Recherche. NMR acquisitions were done at the Laboratoire d’Application de Résonance Magnétique

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Citation Excerpt :
Various methods were reported for the synthesis of imidazoles. 5-Amino-2-thioimidazoles 71 were synthesized by propylphosphonic anhydride (T3P)-mediated cyclization of N-acetamidoisothioureas 70 (15TL1011). An efficient method for the preparation of 1,10-dihydroxy-2,2′-biimidazoles via cyclization of α,α′-dinitrones was reported (15TL159).
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Access to newly functionalized imidazole derivatives: efficient synthesis of novel 5-amino-2-thioimidazoles using propylphosphonic anhydride (®T3P)

Abstract

Graphical abstract

Section snippets

Acknowledgments

Bioorg. Med. Chem. Lett.

Bioorg. Med. Chem. Lett.

Eur. J. Med. Chem.

J. Med. Chem.

Tetrahedron Lett.

Med. Res. Rev.

Curr. Med. Chem.