ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Ca-mediated Nenitzescu synthesis of 5-hydroxyindoles

Arezo Teymori, Anna Sedaghat, and Farzad Kobarfard

Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran

E-mail: Kobarfard@sbmu.ac.ir

Received: 13 May 2022  Accepted: 29 August 2022

Abstract:

Calcium iodide (CaI₂) catalyzes cycloaddition reaction in Nenitzescu synthesis to afford 5-hydroxyindoles from corresponding quinones and enamines. This method introduces CaI₂ as a catalyst in performing this type of condensation reaction for the first time and presents advantages in using nontoxic metal, work-up simplicity, functional group tolerance, and can compete with other methods to overcome the current problems such as low yield and polymerization side reactions.

Graphical abstract

Keywords: Ca-catalyzed; Cycloaddition; 5-Hydroxyindole; Quinone; Calcium iodide; Nenitzescu indole synthesis

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02463-y

Chemical Papers 77 (4) 1791–1795 (2023)