Synthesis of New 4-Oxo-Tetrahydroindol Derivatives by Using Chemical and Microbial Biotransformation Methods

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Caliskan Z., Soydan E., Kurt Gür G., Ordu E.

Polycyclic Aromatic Compounds, vol.40, no.5, pp.1390-1396, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 40 Issue: 5
  • Publication Date: 2020
  • Doi Number: 10.1080/10406638.2018.1553194
  • Journal Name: Polycyclic Aromatic Compounds
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Agricultural & Environmental Science Database, Applied Science & Technology Source, CAB Abstracts, Communication Abstracts, Food Science & Technology Abstracts, Metadex, Pollution Abstracts, Veterinary Science Database, Civil Engineering Abstracts
  • Page Numbers: pp.1390-1396
  • Keywords: Acetoxylation, Aspergillus niger, indole, manganese(III) acetate, MANGANIC ACETATE, INDOLE, DEBENZYLATION, ASPERGILLUS, PURIFICATION, DEGRADATION, OXIDATION
  • Yıldız Technical University Affiliated: Yes

Abstract

© 2019 Taylor & Francis Group, LLC.An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 4-oxo-4,5,6,7-tetrahydroindoles (4) and (5) for the first time. Manganese(III) acetate-mediated acetoxylation of (2) produced 4,5,6,7-tetrahydro-4-oxo-7,7-dimethyl benzofuran-5-yl acetate (3) for the first time in the literature. Then 4,5,6,7-tetrahydro-4-oxo-7,7-dimethyl benzofuran-5-yl acetate was converted to its indole derivative (4) via benzyl amine. Thus, 1-benzyl-5-hydroxy-7,7-dimethyl-6,7-dihydro-1H-indol-4(5H)-one (4) was obtained in good yields. Furthermore, biotransformation of pharmacologically interesting compounds such as 5-hydroxy-7,7-dimethyl-6,7-dihydro-1H-indol-4-(5H)-one (5) were also obtained by biotransformation reaction using Aspergillus niger.