An Efficient Regioselective Access to (11Z)‐11‐(3‐Aryl‐5,6‐dihydropyrazin‐2(1H)‐ylidene)‐11H‐indeno[1,2‐b]quinoxaline Derivatives via One‐Pot Three‐Component Reaction

Abstract

Here we reported an efficient one-pot reaction between 11Hindeno[1,2-b]quinoxalin-11-one, 1-phenyl-2-(1,1,1-triphenyl-λ 5phosphanylidene)ethan-1-one and diamine derivatives to access (11E)-11-(3-aryl-5,6-dihydropyrazin-2(1H)-ylidene)-11Hindeno[1,2-b]quinoxalines. The reaction allows the formation of the desired products under mild and catalyst-free conditions with excellent regioselectivity and high yields (85-95%). All products were characterized by IR, EI-MS, 1 H NMR and 13 C NMR spectroscopic analysis.

One‐Pot Three‐Component Synthesis of Biologically Promising Indenoquinoxaline Fused Spiroheterocycles Starting from 11H‐indeno[1,2‐b]quinoxalin‐11‐ones

“…In 2019, Alizadeh and Roosta [57] reported a facile, catalyst-free, onepot three-component protocol for the synthesis of a series of 11Z)-11-(3-aryl-5,6-dihydropyrazin-2(1H)-ylidene)-11H-indeno[1,2b]quinoxaline derivatives (59) in good yields (85-95 %) from the reactions of 11H-indeno [1,2-b]quinoxalin-11-one (1), 1-phenyl-2-(1,1,1-triphenyl-λ 5 -phosphanylidene)ethan-1-one (57) and ethylenediamine (58) in ethanol at room temperature (Figure 23).…”

Recent Strategies in Transition-Metal-Catalyzed Sequential C–H Activation/Annulation for One-Step Construction of Functionalized Indazole Derivatives

“…Nitrogen-based heterocyclic systems are commonly found in pharmaceutical agents and natural products, and they have been intensively explored as new bioactive products [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. Among them, the indazoles [ 11 , 12 , 13 , 14 , 15 , 16 ] are favored by synthetic and medicinal chemists, as evidenced by their widespread abundance in pharmaceuticals and natural products.…”

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

“…In 2019, Alizadeh and Roosta carried out an efficient one‐pot procedure to build up dihydropyrazine embedded indenoquinoxalines 57 via the reaction of 1‐aryl‐2‐(triphenylphosphoranylidene)ethanone 54 and ethylenediamines 6 . The reaction involves regioselective nucleophilic addition of diamines 6 to the α‐position of α,β‐unsaturated carbonyl compounds 55 followed by cyclization to obtain dihydropyrazine skeleton (Scheme ).This protocol permits the formation of desired products in high yields (85–95 %) under mild, catalyst‐free conditions with excellent regioselectivity and without coumn chromatography.…”