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Angew Chem Int Ed Engl. 2019 Dec 19;58(52):18913-18917. doi: 10.1002/anie.201911156. Epub 2019 Nov 12.

One-Step Synthesis of 2,5-Diaminoimidazoles and Total Synthesis of Methylglyoxal-Derived Imidazolium Crosslink (MODIC).

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1
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT, 06511, USA.

Abstract

Here we describe a general method for the synthesis of 2,5-diaminoimidazoles, which involves a thermal reaction between α-aminoketones and substituted guanylhydrazines without the need for additives. As one of the few known ways to access the 2,5-diaminoimidazole motif, our method greatly expands the number of reported diaminoimidazoles and further supports our previous observations that these compounds spontaneously adopt the non-aromatic 4(H) tautomer. The reaction works successfully on both cyclic and acyclic amino ketone starting materials, as well as a range of substituted guanylhydrazines. Following optimization, the method was applied to the efficient synthesis of the advanced glycation end product (AGE) methylglyoxal-derived imidazolium crosslink (MODIC). We expect that this method will enable rapid access to a variety of biologically important 2,5-diaminoimidazole-containing products.

KEYWORDS:

advanced glycation end products; cyclization; diaminoimidazoles; sigmatropic rearrangement; total synthesis

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