title: Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry.
abstract: 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.
authors: Bioorganic and Medicinal Chemistry Laboratories, Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, United States.
authors: Nadeesha
authors: N
authors: Ranasinghe
authors: Graham B
authors: GB
authors: Jones
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry*; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D005461:Fluorine / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008872:Microwaves; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*; D000077484:Vemurafenib
chemical_list: D000970:Antineoplastic Agents; D007211:Indoles; D010455:Peptides; D013449:Sulfonamides; D000077484:Vemurafenib; D005461:Fluorine; C030374:indole