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

Consecutive Betti/Bargellini multicomponent reactions: an efficient strategy for the synthesis of naphtho[1,2-f][1,4]oxazepine scaffolds

Hassan Farhid, Mohammad Taghi Nazeri, Mohammad Mahdi Rostami, Ahmad Shaabani, and Behrouz Notash

Faculty of Chemistry, Shahid Beheshti University, G.C., Tehran, Iran

E-mail: a-shaabani@sbu.ac.ir

Received: 31 July 2021  Accepted: 5 October 2021

Abstract:

An efficient and convenient approach has been developed for the synthesis of naphtho[1,2-f][1,4]oxazepine structures based on the consecutive Betti/Bargellini multicomponent reactions. Aminobenzylnaphthols were prepared from 2-naphthol, aromatic aldehydes, and 2-aminopyridine via the Betti reaction, and then, naphtho[1,2-f][1,4]oxazepine derivatives were synthesized using the Betti reaction products, chloroform, and aliphatic ketones in the presence of sodium hydroxide via Bargellini multicomponent reactions. A significant aspect of this work is the construction of novel oxazepine-based scaffolds with potential pharmaceutical interest from cheap and readily available starting materials in moderate yields.

Graphic abstract

Keywords: Oxazepines; Betti reaction; Bargellini reaction; Consecutive multicomponent reaction

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01924-0

Chemical Papers 76 (2) 987–993 (2022)