Recyclable Indium(III) Chloride Catalyzed Site-Selective Double Substitution in One Pot for the Synthesis of Isatin N-Ribonucleosides under Microwave Irradiation

Abstract

A novel one-pot synthesis of isatin N-ribonucleosides from N-phenylribosylamines and diethyl oxalate in ethanol catalyzed by recyclable indium(III) chloride under microwave irradiation has been developed. The transformation consists of indium(III) chloride catalyzed nucleophilic substitution by N-phenylribosylamines on diethyl oxalate followed by rapid intramolecular electrophilic substitution, which results in annulation of a five-membered nitrogen heterocycle on to the benzene ring yielding isatin N-ribonucleosides. The reaction proceeded smoothly in quantitative yields at ambient temperatures. The starting materials, N-phenylribosylamines, were prepared by indium(III) chloride catalyzed nucleophilic substitution of the anomeric hydroxy group of b-Dribofuranose by an arylamine under microwave irradiation.

Studies on the chemical behavior of 3-(nitroacetyl)-1-ethyl-4-hydroxyquinolin-2(1H)-one towards some electrophilic and nucleophilic reagents

“…3-(1-Ethyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-2-nitro-3-oxopropanal (9) Phosphoryl chloride (3 mL) was added dropwise with continuous stirring to the pre-cooled dimethylformamide (10 mL) in an ice bath. After complete addition, the mixture was further stirred for 30 min at ambient temperature, then 3-nitroacetyl derivative 4 (1.10 g, 4 mmol) in dimethylformamide (10 mL) was added dropwise with at d 4.93 ppm due the CH 2 NO 2 protons, in addition to eight aromatic protons and ethyl protons.…”

“…[1][2][3][4][5][6] The biological importance of quinolinones stimulated an intensive research work for the synthesis of many members of this class of compounds. [7][8][9][10] In continuation of our previous reports on the synthesis of novel 4-hydroxyquinolin-2(1H)-ones starting from 3-(1-ethy1-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-3-oxopropanoic acid (1), 11 the present work aims to synthesize the 3-(nitroacetyl)-1-ethyl-4-hydroxyquinolin-2(1H)-one (4) and to study its reactivity towards a variety of chemical reagents.…”

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

“…On the basis of environmental consideration, InCl 3 alone and In/InCl 3 system applied in aqueous media for the synthesis of fused pyrimidines and pyrazoles [28] and indium homoenolate (organoindium complex) [29] respectively. Moreover, InCl 3 can be recycled after the synthesis of isatin N ‐ribonucleosides [30] from N ‐phenylribosylamines and diethyl oxalate under microwave irradiation. Condensation reaction between different dialdehydes and pyrroles to synthesize various bis(dipyrromethanes), [31] and preparation of 1,8‐dioxo‐decahydroacridines [32] from aldehydes, 1,3‐diketones with aromatic amines or ammonium acetate catalyzed by InCl 3 has a great inclusion in organic chemistry.…”

[bmim]OH promoted hydroalkynylation of nitrile and intramolecular hydroamination of the carbon–carbon multiple bond: an efficient and eco-compatible strategy for the synthesis of indolizinones

“…ILs are reported to have displayed significant roles as catalysts, reaction media and reagents and are easy to recover and reuse. [13][14][15] Buoyed from the above facts and to circumvent the abovementioned drawbacks, as well as a part of our ongoing endeavour for the construction of simple, efficient, versatile synthetic methodologies for biodynamic heterocyclic scaffolds, [16][17][18][19][20][21][22] we have developed an eco-compatible, facile and atom economical methodology using 2-cyanopyridine and phenylacetylene as reactants, [bmim]OH as an alternative reaction medium and promoter, and microwave activation as an alternative energy source to furnish indolizinones in 72-98% yield (Scheme 1).…”