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Bioorg Med Chem Lett. 2013 Mar 15;23(6):1740-2. doi: 10.1016/j.bmcl.2013.01.066. Epub 2013 Jan 26.

Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry.

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  • 1Bioorganic and Medicinal Chemistry Laboratories, Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, United States.


Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags.

Copyright © 2013 Elsevier Ltd. All rights reserved.

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