Selective Synthesis of Mono‐ and Disubstituted Quinoxalines via Heteroaromatic Nucleophilic Substitution of 2, 3‐Dichloro‐6, 7‐dinitroquinoxaline (DCDNQX) with Anilines and Phenols. Issue 38 (16th October 2018)

• Record Type: Journal Article
• Authors: de O. Lima Filho, Edson; da S. Ribeiro, Stephany L.; Araújo, Renata M.; Menezes, Fabrício G.; Cavalcanti, Lívia N.
• Is Part Of: ChemistrySelect. Volume 3:Issue 38(2018)
• Page Start: 10782
• Page End: 10786
• Publication Date: 2018-10-16
• Subjects: DCDNQX -- heterocycles -- quinoxaline -- SNAr -- synthesis; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201802582
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: The chemistry of quinoxalines has attracted great attention due to the potential applications of this class of nitrogen‐based heterocycle in many areas. In this paper, heteroaromatic nucleophilic substitution of the quinoxaline substrate 2, 3‐dichloro‐6, 7‐dinitroquinoxaline (DCDNQX) with anilines and phenols is reported. Reactions using this reagent were proven to proceed under mild and metal‐free conditions for selectively obtaining mono and disubstituted products in good to excellent yields. Abstract : Selective synthesis of mono and di‐substituted quinoxalines via SN Ar with anilines and phenols as nucleophiles was performed using 2, 3‐dichloro‐6, 7‐dinitroquinoxaline (DCDNQX). The DCDNQX substrate has proven to be of great synthetic value, allowing selectivity control of under mild and metal free reaction conditions. The products synthesized in this work are, to the best of our knowledge, unprecedented in the literature.