A ONE-POT THIOMETHYLATION OF PYRROLE AND INDOLES

Authors

  • Vnira R. Akhmetova Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 Oktyabrya Ave., Ufa 450075
  • Danil V. Leont'ev Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 Oktyabrya Ave., Ufa 450075
  • El'mira M. Galimova Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 Oktyabrya Ave., Ufa 450075
  • Ekaterina S. Mescheryakova Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 Oktyabrya Ave., Ufa 450075

Keywords:

formaldehyde, heteroauxin, indole, pyrrole, tryptophan, S-nucleophile, one-pot synthesis, thiomethylation

Abstract

C(sp2)H functionalization of pyrrole, indole, indolyl-3-acetic acid (heteroauxin), and 2-amino-3-(indol-3-yl)propionic acid (tryptophan) was carried out via a one-pot C-thiomethylation with formaldehyde and mercaptans in pyridine which simultaneously played the role of a catalyst and solvent. The possibility of the synthesis of structurally diverse sulfanyl methylindoles depending on the nature of the reagents was demonstrated.

Author Biographies

Vnira R. Akhmetova, Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 Oktyabrya Ave., Ufa 450075

Лаборатория гетероатомных соединений, д.х.н., зав. лаб. гетероатомных соединений

Danil V. Leont'ev, Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 Oktyabrya Ave., Ufa 450075

Лаборатория гетероатомных соединений, аспирант

El'mira M. Galimova, Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 Oktyabrya Ave., Ufa 450075

Лаборатория молекулярного дизайна и биологического скриннинга веществ-кандидатов для фарминдустрии ИНК УФИЦ РАН, м.н.с.

Ekaterina S. Mescheryakova, Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 Oktyabrya Ave., Ufa 450075

лаборатория структурной химии, к.х.н., н.с.

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Published

2024-01-10

Issue

Vol. 59 No. 11/12 (2023)

Section

Original Papers