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Benzofuran-2-Carbohydrazides Via Greener Approach and Their Biological Activities

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Benzofuran-2-Carbohydrazides Via Greener Approach and Their Biological Activities Available online a t www.derpharmachemica.com Scholars Research Library Der Pharma Chemica, 2014, 6(1):272-278 (http://derpharmachemica.com/archive.html) ISSN 0975-413X CODEN (USA): PCHHAX Synthesis of novel N ′-(2-oxoindolin-3-ylidene)benzofuran-2-carbohydrazides via greener approach and their biological activities Bharti Bhardwaj* and Subhash C. Jain Department of Chemistry, University of Delhi, Delhi, India _____________________________________________________________________________________________ ABSTRACT A novel series of N′-(2-oxoindolin-3-ylidene)benzofuran-2-carbohydrazides was synthesized starting from substituted indoline-2,3-diones and benzofuran-2-carbohydrazide. The reaction was performed in water and the procedure was very simple and clean, as no use of any organic solvent or catalyst. This provides new opportunities for the rapid screening of a wide range of compounds, either for the development of new drugs, or original compounds for the material scientist. All the synthesized compounds were fully characterized on the basis of their detailed spectral studies and were also evaluated for their biological activities. Keywords: Aqueous medium, Benzo[ b]furan, Condensation reaction, Hydrazones, Indoline-2,3-diones _____________________________________________________________________________________________ INTRODUCTION The environmental protection has become a global concern these days and therefore the synthetic organic chemists are searching the ways of developing and applying more efficient and environmentally benign strategies for sustainable future growth. One of the thrust areas for achieving this target is use of Green Chemistry Techniques in Organic Synthesis. Heterocyclic hydrazones constitute an important class of biologically active drug molecules which have attracted attention of medicinal chemists due to their wide ranging pharmacological properties [1]. They are also key intermediates for many reactions and also for the preparation of heterocyclic rings [2]. At present a broad range of methods for synthesizing imines [3] in the presence of catalysts are available: ZnCl 2 [4], TiCl 2 [5], K- 10 [6], MgSO 4-PPTL [7] Mg(ClO 4)2 [8] and also SiO 2–NaHSO 4 (under MW irradiation condition) [9]. More recently, ultrasound irradiation has been used to give rise to the formation of a series of Schiff bases (aryl–aryl and aryl–alkyl), under solvent-free conditions [10] or using SiO 2 as a catalyst in ethanol [11] with short reaction times (10–20 min) and high yields. For aryl-hydrazones, most reaction methods described to date involve the use of methanol as a solvent without catalysts at reflux, although ethanol and acid catalysis (or p-toluenesulfonic acid in dried toluene) are required if the carbonyl compounds bear a strong electron-withdrawing group [12]. Benzo[ b]furan is a class of compound which is widely distributed in nature [13, 14] and its compound shown varied biological activities [15-18]. Over the last few years Benzo[ b]furan and its derivatives has drawn considerable attention due to their profound physiological and chemotherapeutic properties such as antibacterial [19] anti-inflammatory [20] and antifungal [21]. On the other hand, indoline-2,3-dione (isatin) is a very biological active molecule containing indole as a core nucleus and known to show proconvulsant [22], anticonvulsant [23], and CNS depressant [24] activities. Isatin derivatives also possess antibacterial [25], anti-inflammatory [26], analgesic [27], anti-viral [28], antifungal [29], anti-tubercular [30] and anti-depressant [31]. So, in view of all the above observations and our interest in developing new heterocycles we have designed and synthesized some new heterocyclic hydrazone derivatives bearing benzofuran and isatin in the same molecule using water as a solvent. The reaction was carried out in very short reaction time i.e. only simple refluxing condition for 20-30 min gave the product in high yield. 272 www.scholarsresearchlibrary.com Bharti Bhardwaj and Subhash C. Jain Der Pharma Chemica, 2014, 6 (1):272-278 ___________________ __________________________________________________________ MATERIALS AND METHODS All the chemicals, reagents and solvents used were obtained from commercial sources and of analytical grade. All the reaction were monitored by thin layer chromatography (TLC) using silica gel G as stationary phase, different solvent systems as mobile phase and iodine vapours as detecting agent. Melting points were determined on an electronic apparatus and are uncorrected. IR spectra were recorded on Shimadzu model IR-435 spectrophotometer using KBr discs for solids and thin films for liquids. 1H NMR and 13 C NMR spectra were recorded on Jeol AC (400 MHz) and Jeol AC (100 MHz) respectively in DMSO-d6 and CDCl 3 using tetramethylsilane (TMS) as an internal standard. TOF ES+ Mass spectra (m/z) were recorded on Micromass Autospec LCTKC455. Substituted indol-2,3- diones were prepared by literature procedures [32], starting from the corresponding aniline and the other reactant benzofuran-2-carboxylic acid hydrazide was prepared in two steps by following the literature procedure [33]. Synthesis of ethylbenzofuran-2-carboxylate (2) To a cooled solution of freshly ignited potassium carbonate (34.0 g) in 50 mL of dry dimethylformamide, a solution of 2-hydroxy benzaldehyde (1) (10 g, 81.96 mmol) in 10 mL of dry dimethylformamide was added dropwise under inert atomosphere of nitrogen. The contents were allowed to stirr at room temperature and then a solution of ethylbromoacetate (13.68 g, 81.96 mmol) in 20 mL of DMF was added to it dropwise. Stirring was continued for additional 20 minutes at this temperature. The contents were then allowed to reflux for 2 h. The progress of the reaction was monitored by using thin layer chromatography. After completion of the reaction, the reaction mixture was cooled and quenched with ice cold water and extracted with ethylacetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure to yield the desired -1 compound 2 as yellow oil. Yield 83%; IR (film, cm )νmax : 2983, 2937, 1729, 1573, 1508, 1466, 1447, 1370, 1346, 1 1298, 1183, 1097, 1018, 946, 868; H NMR ( δ, CDCl 3, 400 MHz): 7.64 (d, 1H, J=7.42 Hz), 7.56 (d, 1H, J=8.08 13 Hz), 7.50 (s, 1H), 7.43-7.41 (m, 1H), 7.28-7.26 (m, 1H), 4.42 (q, 2H), 1.40 (t, 3H); C NMR ( δ, CDCl 3, 100 MHz): 159.5, 155.6, 145.6, 127.5, 126.8, 123.6, 122.7, 113.7, 112.2, 61.4, 14.2; Mass spectral data, TOF ES+ m/z (%): 191 (M ++1). Synthesis of benzofuran-2-carboxylic acid hydrazide (3) The mixture of hydrazine hydrate (15 ml) and ethyl benzofuran-2-carboxylate ( 2) (2.28 g, 12 mmol) was stirred at 0- 5°C for 30 min. The reaction was monitored by using thin layer chromatography. Further, the reaction mixture was stirred at room temperature to give benzofuran-2-carbohydrazide (3) as a white colored shining product. Yield 89%, -1 1 mp 190-194 °C; IR (KBr, cm )νmax : 3322, 3182, 3023, 2975, 1659, 1546, 1328, 1187, 1089, 822, 735; H NMR ( δ, DMSO-d6, 400 MHz): 9.31 (s, 1H, >NH, D 2O exchangeable), 7.69 (d, 1H, J = 8.0 Hz), 7.54 (d, 1H, J = 7.44 Hz), 13 7.49 (s, 1H), 7.44-7.40 (m, 1H), 7.32-7.29 (m, 1H), 4.26 (brs, 2H, -NH 2, D2O exchangeable); C NMR ( δ, DMSO- d6, 100 MHz): 159.8, 154.8, 147.3, 127.2, 123.8, 122.7, 111.8, 111.0; Mass spectral data, TOF ES+ m/z (%): 177 (M ++1). General procedure for the synthesis of N ′-(2-oxoindolin-3-ylidene)benzofuran-2-carbohydrazides ( 5a-j) To the solution of benzofuran-2-carboxylic acid hydrazide (3) (176 mg, 1.0 mmol) in water (20 mL), indoline-2,3- dione/ substituted indoline-2,3-dione was added and the reaction mixture was refluxed. Progress of the reaction was monitored on thin layer chromatography. A solid that separated out was filtered and dried to yield the corresponding hydrazone. N′-(5-Methyl-2-oxoindolin-3-ylidene)benzofuran-2-carbohydrazide (5a) -1 1 Yield 95%; m.p. >280 °C; IR (KBr, cm )νmax : 3440, 3216, 2925, 1721, 1665, 1600, 1541, 1481, 1311, 876, 745; H NMR (δ, DMSO-d6, 400 MHz): 11.72 (s, 1H, -NH, D 2O exchangeable), 10.74 (s, 1H, >NH, indole, D 2O exchangeable), 8.04 (s, 1H), 7.89-7.83 (m, 2H), 7.73 (d, 1H, J=8.72 Hz), 7.56-7.52 (m, 1H), 7.41-7.37 (m, 1H), 7.24 (d, 1H, J=8.02 13 Hz), 6.87-6.80 (m, 1H), 2.33 (s, 3H); C NMR ( δ, DMSO-d6, 100 MHz): 165.2, 164.8, 155.0, 147.0, 142.4, 140.9, 133.8, 131.2, 128.2, 127.4, 124.4, 123.7, 120.0, 121.9, 115.8, 112.4, 111.0, 21.1; Mass spectral data, TOF ES+ m/z (%): 320 (M ++1). N′-(2-Oxoindolin-3-ylidene)benzofuran-2-carbohydrazide (5b) -1 Yield 96%; m.p. >280 °C; IR (KBr, cm )νmax : 3445, 3234, 2926, 1720, 1668, 1606, 1578, 1340, 1259, 1164, 1009, 1 941, 873, 745; H NMR ( δ, DMSO-d6, 400 MHz): 11.73 (s, 1H, -NH, D2O exchangeable), 10.83 (s,1H,>NH, indole, D2Oexchangeable), 8.02 (s, 1H), 7.86 (m, 2H), 7.76 (d, 1H, J = 8.04 Hz), 7.57-7.52 (m, 1H), 7.44-7.37 (m, 2H), 13 7.13-7.09 (m, 1H), 6.98-6.92 (m, 1H); C NMR ( δ, DMSO-d6, 100 MHz): 164.9, 163.2, 154.7, 142.7, 131.4, 127.6, 126.1, 125.5, 124.8, 123.7, 122.3, 121.5, 120.3, 114.2, 111.9, 110.4, 109.3; Mass spectral data, TOF ES+ m/z (%): 306 (M ++1).
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