Route to pyrrolo[1, 2-a]quinoxalines via a furan ring opening-pyrrole ring closure sequence. Issue 9 (27th February 2020)

• Record Type: Journal Article
• Authors: Zelina, Elena Y.; Nevolina, Tatyana A.; Sorotskaja, Ludmila N.; Skvortsov, Dmitry A.; Trushkov, Igor V.; Uchuskin, Maxim G.
• Is Part Of: Tetrahedron letters. Volume 61:Issue 9(2020)
• Publication Date: 2020-02-27
• Subjects: Furan -- Pyrrolo[1, 2-a]quinoxaline -- Paal-Knorr synthesis -- 1, 4-Diketone -- Domino reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151532
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Route for the synthesis of functionalized pyrrolo[1, 2- a ]quinoxalines was developed. The hydrolysis of N -protected furfurylamines produced 1, 4-diketones in high yields. The reductive Paal-Knorr reaction afforded the target pyrrolo[1, 2- a ]quinoxalines. The cytotoxicity of obtained pyrrolo[1, 2- a ]quinoxalines was investigated. Abstract: A method was developed for the synthesis of pyrrolo[1, 2- a ]quinoxalines based on an acid-promoted furan ring opening of readily accessible N -(furan-2-ylmethyl)-2-nitroanilines or their heterocyclic analogues followed by a key reductive Paal-Knorr cyclization of the corresponding nitro-1, 4-diketones.