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A Green Synthesis of Quinoxaline Derivatives & Their Biological Actives

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A Green Synthesis of Quinoxaline Derivatives & Their Biological Actives International Journal of Applied Chemistry. ISSN 0973-1792 Volume 13, Number 3 (2017) pp. 421-432 © Research India Publications http://www.ripublication.com A green synthesis of quinoxaline derivatives & their biological actives Kiran Ga*, Laxminarayana Eb, Thirumala Chary Mc and Ravinder Ma aChaithanya PG College, Kishanpura, Warangal, India. bSreenidhi Institute of Science and Technology (Autonomous), Yamnampet, Ghatkesar Hyderabad-501301 Telangana, India. cJawaharlal Nehru Techological University Hyderabad 500085 Telangana, India. *Corresponding author Abstract A simple and catalyst free synthetic method has been developed by the synthesis of quinoxaline derivatives from 2-chloro quinoxaline and different types of amine derivatives using PEG-400 green solvent at room temperature. This method is simple, ecofriendly, rapid-generates 2-amino quinoxaline derivatives and good yield without use any catalysts. PEG-400 increases the rate of reaction and reduces reaction time. Newly synthesized compounds were screened for their antibacterial activity against Escherichia coli, Bacillus subtilis, Pseudomonas, Staphylococcus aureus. The structure of quinoxaline derivatives were confirmed by using IR, 1H-NMR, Mass spectroscopy. Keywords: 2-chloro quinoxaline, Catalyst free, Green synthesis, PEG-400. INTRODUCTION: Quinoxaline derivatives are an important class of heterocyclic compounds. It is rare in natural state, but their synthesis is easily to perform1. Quinoxaline molecular formula is C8N2H6 and is formed by two aromatic rings, benzene and pyrazine. In quinoxaline pyrazine ring is water soluble and stable colourless compound. Benzene ring is fused with diazines compounds. The pyrazine ring system is present in the fungal metabolite aspergillic acid and also in luciferin. Methoxy pyrazine are essential component of aroma of many fruits and vegetables such as capsicum and peas2. In quinoxaline 6-membered nitrogen heterocyclies containing two nitrogens in 422 Kiran G, Laxminarayana E, Thirumala Chary M and Ravinder M mutually para dispositions.These compounds have a wide range of applications in bacteriology, pharmacology and mycology3-7, Quinoxaline derivatives continued to be of great interest due to a wide spectrum of their biological activity such as actinolutin, echinomycin and levomycin that are know to inhibit growtth of gram positive bacteria8-9, anti fungal10-11, anti convulsant12, anti depressant13-14, anti neoplastic15-17, anti viral18, anti bacterial19-21, anti inflammatory22, anti malarial activity23, anti HIV activity24, quinoxaline derivatives are also used in dyes, organic semiconductor, cavitands and dehydroannulenes. Quinoxaline are important in industry also due to their ability to inhibit metal corrosion25-27. Polyethylene glycol-40028, as an efficient reaction medium for preparation of quinoxaline derivatives containing nitrogen cyclic ring system. PEG-400 used in many organic reactions for conversion29 of oxiranes to thiranes, asymmetric aldol reactions30 in presence of L-Proline, cross-coupling reaction,31 Baylis-Hillman reaction32 and ring opening of epoxides.33 We now designed and synthesized a series of novel quinoxaline derivatives from 2- chloro quinoxaline by applying the principles of green chemistry using PEG-400 as an alternative reaction medium. PEG is an eco-friendly reaction solvent. PEG-400 is non-toxic, Inexpensive, potentially recyclable and water soluble, which facilitates it is easily removal from the reaction product. EXPERIMENTAL: All the chemicals were used as purchased from sigma-aldrich, Avra Laboratories. Solvents and reagents were obtained from commercial sources. Melting Points are uncorrected and were determined using open capillary tubes in sulfuric acid bath. TLC analyses were done on plastic sheets coated with silica gel G and spotting was done using Iodine/UV lamp. IR spectra were recorded on a Perkin Elmer model 1000 1 13 instrument in KBr Pellet. H-NMR and C NMR were recorded in CDCl3/DMSO-d6 using 400 MHZ and 100 MHz varian Gemini spectrometer and TMS as a reference standard. Mass spectra were recorded on an Agilent-LCMS instrument. General procedure for the preparation of 4a : A mixture of 3(10 mmol, 1eq), 6-Benzyl amino purine (10 mmol, 1eq), K2CO3(1.67g, 20mmol, 2eq), KI(0.3g, 3mmol, 0.3eq) and different solvent such as Acetonitrile/1,4Dioxane/THF/EToH/MeOH/DMF was heated at 800C-1000C for 2-6 hr. The progress of reaction was monitored by TLC, after completion of reaction, mixture was diluted with water and extracted with E.A(2x25mL). The combined organic layer was washed with water, brine and then dried with anhydrous Na2So4. The organic layer was distilled under reduced pressure, gave respectively 4a(scheme A green synthesis of quinoxaline derivatives & their biological actives 423 1, Table 1). General procedure for the preparation of 4(a-j) under PEG-400 : A Mixture of powderad anhydrous K2CO3 (1.67g, 20mmol, 2eq), PEG-400, KI(0.3g, 3mmol, 0.3eq) and 6-Benzyl amino purine/different amine derivatives (10 mmol, 1.0eq) was taken in a mortar and ground with a pestle for few minutes. To this mixture, starting material 3(10mmol, 1.0eq) was added and the whole mixture was ground with pestle in the mortar at room temperature. After sometime monitored by TLC after then, mixture was treated with ice-cold water(50 mL). product separated by filteration, washed with water, and dried to obtain products of 4(a-j) [scheme 1, Table 2]. Quinoxaline-2-ol: (2) 1 ( H NMR (400 MHz, CDCl3): 12.3ppm (s, 1H, Ar-OH), 7.91(d, 1H, Ar-H), 7.74(t, 1H, Ar-H), 7.74(t, 1H, Ar-H), 7.91(d, 1H, Ar-H), 8.16(s, 1H, Ar-H); 13C NMR (100 MHz, CDCl3): (175.4, 142.4, 138.5, 135.4, 129.8, 128.6, 126.4, 122.5; LC-MS m/z, 147.19 [M+H]+. 2-chloro quinoxaline: (3) 1 H NMR(400MHz, CDCl3): 8.16 (s, 1H, Ar-H), 7.91(d, 1H, Ar-H), 7.74(t, 1H, Ar-H), 13 7.74(t,1H, Ar-H), 7.91(d, 1H, Ar-H); C NMR (100 MHz, CDCl3): (175.9, 143.5, 136.9, 133.4, 130.1, 127.6, 125.4, 123; LC-MS m/z, 165.59 [M+H]+. N-benzyl-N-(7H-purin-6-yl)quinoxalin-2-amine: (4a) 1 H NMR (400 MHz, CDCl3): 8.16 (s, 1H, Ar-H), 12.09(d, 1H, Ar-NH), 7.91(d, 1H, Ar-H), 7.74(t, 1H, Ar-H), 7.74(t, 1H, Ar-H), 7.91(d, 1H, Ar-H), 4.24(s, 2H, CH2), 7.16(d, 1H, Ar-H), 7.28(t, 1H, Ar-H), 7.20(t, 1H, Ar-H), 7.28(t, 1H, Ar-H), 7.16(d, 13 1H, Ar-H), 8.09(s, 1H, Ar-H), 8.21(d, 1H, Ar-H), C NMR (100 MHz, CDCl3) : (175.9, 164.5, 156, 152.7, 149, 138.7, 136.1, 133, 131.5, 130.6, 129.4, 127.3, 126.8, 126.2, 125.3, 124.9, 124, 123.2, 120.4, 59.1; LC-MS m/z, 354.14 [M+H]+. 4-(quinoxalin-2-yl ) morpholine: (4b) 1 H NMR (400 MHz, CDCl3): 8.16 (s, 1H, Ar-H), 7.91(d, 1H, Ar-H), 7.74(t, 1H, Ar- H), 7.74(t, 1H, Ar-H), 7.91(d, 1H, Ar-H), 3.89(t, 2H, CH2), 3.79(t, 2H, CH2), 3.79(t, 13 2H, CH2), 3.89(t, 2H, CH2); C NMR (100 MHz, CDCl3) : 169.1, 142.3, 136, 132.4, 129.8, 127.4, 124.2, 121.6, 68.6, 68.6, 49.4, 49.4; LC-MS m/z, 216.11 [M+H]+. 2-(piperidin-1-yl) quinoxaline: (4c) 1 H NMR (400 MHz, CDCl3): 8.16 (s, 1H, Ar-H), 7.91(d, 1H, Ar-H), 7.74(t, 1H, Ar- H), 7.74(t, 1H, Ar-H), 7.91(d, 1H, Ar-H), 3.95(t, 2H, CH2), 1.71(m, 2H, CH2,), 13 1.83(m, 2H, CH2), 1.71(m, 2H, CH2), 3.95(t, 2H, CH2); C NMR (100 MHz, 424 Kiran G, Laxminarayana E, Thirumala Chary M and Ravinder M CDCl3): 169.1, 142.3, 136, 132.4, 129.8, 127.4, 124.2, 121.6, 55.3, 30.9, 27.4, 30.9, 55.3; LC-MS m/z, 214.13 [M+H]+. 2-(piperazin-1-yl) quinoxaline: (4d) 1 H NMR(400 MHz, CDCl3): 8.16 (s, 1H, Ar-H), 7.91(d, 1H, Ar-H), 7.74(t, 1H, Ar- H), 7.74(t, 1H, Ar-H), 7.91(d, 1H, Ar-H), 3.59(t, 2H, CH2), 3.01(m, 2H, CH2), 13 3.01(m, 2H, CH2), 3.59(t, 2H, CH2), 2.1(m, 1H, NH). C NMR(100 MHz, CDCl3): 169.1, 142.3, 136, 132.4, 129.8, 127.4, 124.2, 121.6, 53.9, 49.7, 49.7, 53.9. LC-MS m/z, 215.27 [M+H]+. 2-(pyrrolidin-1-yl) quinoxaline: (4e) 1 H NMR(400 MHz, CDCl3): 8.16(s, 1H, Ar-H), 7.91(d, 1H, Ar-H), 7.74(t, 1H, Ar- H), 7.74(t, 1H, Ar-H), 7.91(d, 1H, Ar-H), 3.07(t, 2H, HN-CH2), 1.69(m, 2H, CH2), 13 1.69(m, 2H, CH2), 3.07(t, 2H, HN-CH2); C NMR(100 MHz, CDCl3): 169.1, 142.3, 136, 132.4, 129.8, 127.4 124.2, 121.6, 60.1, 30.4, 30.4, 60.1; LC-MS m/z, 200.21 [M+H]+. 2-(4-methylpiperazin-1-yl) quinoxaline: (4f) 1 H NMR(400 MHz, CDCl3): 8.16(s, 1H, Ar-H), 7.91(d, 1H, Ar-H), 7.74(t, 1H, Ar-H), 7.74(t, 1H, Ar-H), 7.91(d, 1H, Ar-H), 3.91(t, 2H, CH2), 2.58(t,2H, CH2), 2.10(s, 3H, 13 N-CH3), 2.58(t, 2H, CH2), 3.91(t, 2H, CH2): C NMR(100 MHz CDCl3): 169.1, 142.3, 136.0, 132.4, 129.8, 127.4, 124.2, 121.6, 49, 58.7, 44.3, 58.7, 49; LC-MS m/z, 229.54 [M+H]+.
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