Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds

Abstract

alpha-hydroxy ketones undergo manganese dioxide-mediated oxidation followed by in situ trapping with aromatic or aliphatic 1,2-diamines to give quinoxalines or dihydropyrazines, respectively, in a one-pot procedure which avoids the need to isolate the highly reactive dicarbonyl intermediates. The scope and limitations of these procedures are outlined and modifications to this procedure are discussed in which reduction is carried out in the same reaction vessel, generating piperazines, or oxidation, leading to pyrazines.

Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts

“…However, the handling of highly reactive dicarbonyl compounds is an important drawback. Other synthesis methods involving 1,4-addition of 1,2-diamines to diazenylbutenes [34], oxidation-trapping of α-hydroxycarbonyl compounds with 1,2-diamines [35][36][37][38], cyclization-oxidation of phenacyl bromides and 1,2-phenylenediamines through solid-phase synthesis [39] and oxidative coupling of epoxides with ene-1,2-diamines [40] have been developed for the synthesis of substituted quinoxalines. Unfortunately, most of these methods suffer from unsatisfactory yields, difficult experimental procedures, the use of expensive and detrimental metal precursors, or demanding reaction conditions.…”

Synthesis of some New Quinoxalines Bearing Pyridinyl Thiazole Moiety

“…5H 2 0 [28], Zn/L-Proline [29] and CAN [30] have been explored. Oxidative couplings of epoxides and ene-1,2-diamines [31] catalyzed by Bi(0), Pd(OAc) 2 , RuCl 2 -(PPh 3 ) 3 -TEMPO, and MnO 2 have been reported [32][33][34]. The condensation has also been accomplished under catalyst-free conditions, but needs microwave heating [35].…”

Recent Advances in Biomimetic Synthesis Involving Cyclodextrins

“…In general many synthetic protocals have been developed for the preparation of quinoxaline derivatives. These include condensation of 1,2-diamines and 1,2-dicarbonyl compounds (Brown, 2004),1,4-addition of 1,2-diamines to diazenylbutenes (Aparicio et al,2006), oxidative coupling of epoxides with ene-1,2-diamines (Antoniotti & Dunach, 2002), oxidative cyclization of α-hydroxy ketones with 1,2-diamines ( Raw et al, 2004;Kim et al, 2005;Robinson & Taylor, 2005;, cyclization-oxidation of phenacyl bromides with 1,2-diamines by HClO 4 .SiO 2 (Das et al, 2007) and by using solid phase synthesis (Wu & Ede,2001;Singh et al, 2003). Existing synthetic methodologies for quinoxaline system are rather limited in number and model when compared to their broad spectrum utility.…”