An efficient method for the synthesis of quinoxaline derivatives catalyzed by titanium silicate-1
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An efficient method for the synthesis of quinoxaline derivatives catalyzed by titanium silicate‑1 Pranav S. Chandrachood1,2 · Amol R. Jadhav2 · Dinesh R. Garud2 · Nirmala R. Deshpande1 · Vedavati G. Puranik3 · Rajashree V. Kashalkar1,2 Received: 24 April 2020 / Accepted: 26 August 2020 © Springer Nature B.V. 2020
Abstract A series of quinoxaline derivatives were efficiently synthesized by convenient and simple procedure in excellent yields using 1 wt.% of titanium silicate (TS-1) catalyzed reaction of 1,2-diamines and 1,2-diketones in methanol at room temperature. This reaction is scalable to multigram scale and the catalyst is recyclable. Graphic abstract
NH2 R NH2
O
R'
+ O
R'
TS-1Catalyst (1 wt%)
N
R'
R
MeOH, rt
N
R'
Keywords Quinoxaline · Titanium silicate-1 · o-phenylenediamine · Aromatic 1,2-diketones · Room temperature
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04258-w) contains supplementary material, which is available to authorized users. * Dinesh R. Garud [email protected] Extended author information available on the last page of the article
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Introduction In recent years, N-containing heterocyclic compounds are the most valuable group of scaffolds in pharmaceuticals and bioactive natural products [1]. In this regard, quinoxalines [2, 3] are a versatile class of nitrogen-containing heterocyclic compounds of pharmacological importance due to its interesting biological activities (Fig. 1) such as antiviral, antibiotic, anti-inflammatory, antiprotozoal, antihelmintic, antimalarial, antitubercular, antidepressant, kinase inhibitors, anticancer and also active against AIDS. Besides the biological activities, quinoxaline derivatives have been reported for their applications in synthesis of organic semiconductors [4–6], dyes [7], and electroluminescent materials [8]. Due to their enormous applications in various fields, a number of synthetic strategies have been developed for the preparation of substituted quinoxalines. Most significant method for the synthesis of quinoxaline includes the condensation of an aryl 1,2-diamine with a 1,2-diketone in the presence of catalysts (or reagents) such as in refluxing ethanol or acetic acid [9], in MeOH=AcOH under microwave irradiation [10], in the presence of catalysts such as molecular iodine [11, 12], cerium ammonium nitrate [13–15], glycerine–cerium chloride [16], sulfamic acid [17], polymer-supported sulphanilic acid [18], Yb(OTf)3 [19], oxalic acid [20], o-iodoxybenzoic acid (IBX) [21], H6P2W18O62.24H2O [22], KHSO4 [23], Ni-nanoparticles [24], nano-Y-Fe2O3-SO3H [25], nanostructured Na2PdP2O7 [26], polyaniline-sulfate salt [27], InCl3 [28], MnCl2 [29], CuSO4.5H2O [30], Zn=Lproline [31], tween 40 [32], HClO4.SiO2 [33], ZnO-loaded mesoporous silica (KIT-6) [34], graphite [35], montmorillonite K-10 [36], Yb-modified NaY zeolite H3C
O N
O N
N H
O N
O
N
O NH2
Cl
N N
O O
XK 469 (NSC697887)
HN
N H
CH3 COOH
O O H3C
CH3
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