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

Synthesis of new benzothiazoles, benzoxazoles, and benzo [1, 3]-dithiols by Ullmann coupling of dihalobenzene and nitro compounds-heterocumulene adducts

Manijeh Nematpour

Department of Chemistry Education, Farhangian University, Tehran, Iran

E-mail: M.nematpour@cfu.ac.ir

Received: 28 June 2024  Accepted: 27 December 2024

Abstract:

In this contribution, a simple and fast method for the synthesis of various types of benzothiazoles, benzoxazoles, and benzo[1,3]-dithioles using Ullman coupling reaction of dihalobenzene and nitro-heterocumulene compounds in the vicinity of copper catalyst, Cs₂CO₃ as the base, and highly efficient was successfully implemented without the help of an additional ligand under ultrasound irradiation. The use of simple and readily available starting materials, mild copper-catalytic reaction conditions, no column chromatography, good yields, applying the sonochemical methodology, and short reaction times are remarkable specifications of this protocol.

Graphical abstract

Keywords: Ullmann coupling; Nitro compounds; Heterocumulene; Dihalobenzene; Ultrasound; Irradiation

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-024-03878-5

Chemical Papers 79 (3) 1627–1635 (2025)