期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 52, 页码 18913-18917出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201911156
关键词
advanced glycation end products; cyclization; diaminoimidazoles; sigmatropic rearrangement; total synthesis
资金
- SENS Research Foundation
- American Diabetes Association Pathway to Stop Diabetes Grant [1-17-VSN-04]
Here we describe a general method for the synthesis of 2,5-diaminoimidazoles, which involves a thermal reaction between alpha-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.
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