Chinese Chemical Letters  2016, Vol.27 Issue (01): 119-126   PDF    
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Hadi Taghrir, Majid Ghashang, Mohammad Najafi Biregan.Preparation of 1-amidoalkyl-2-naphthol derivatives using barium phosphate nano-powders[J]. Chin. Chem. Lett., 2016,27(01): 119-126  
Preparation of 1-amidoalkyl-2-naphthol derivatives using barium phosphate nano-powders
Hadi Taghrira, Majid Ghashangb , Mohammad Najafi Bireganb    
a Department of Chemistry, Science and Research Branch, Islamic Azad University, Arak, Iran;
b Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Iran
Received: 2015-04-09, Revised: 2015-07-21, online: 2015-08-20.
E-mail addresses: ghashangmajid@gmail.com
Abstract: Barium phosphate(Ba3(PO4)2) nano-powder was successfully synthesized via a simple precipitation route without any surfactant. The prepared nano-powder was applied for the facile synthesis of 1-amidoalkyl-2-naphthol derivatives using multi-component reaction of aldehydes, 2-naphthol and an amide(or urea) in high yields.
Key words: Multi-component reaction     1-Amidoalkyl-2-naphthol     Barium phosphate(Ba3(PO4)2)     2-Hydroxydibenzofuran    
1. Introduction

Establishing methods to synthesize 1,3-amino oxygenated functional groups is an immensely important pursuit in organic synthesis due to the role of this functional group as an antibiotic, HIV protease inhibitor and building block in a many biomolecules as well as pharmaceutically interesting compounds [1, 2, 3]. 1- Amidoalkyl-2-naphthols are a class of these molecules that are prepared via multi-component reaction of aldehydes,2-naphthol, and an amide (or urea). Several Lewis and Brønsted acidic catalysts have been used for this transformation,including montmorillonite K10 [4],Ce(SO4)2 [5],I2 [6],K5CoW12O40.3H2O [7],p-TSA [8], ultrasound-promoted sulfamic acid [9],zirconyl(IV) chloride [10], silica sulfuric acid [11],cation-exchanged resins [12],sulphamic acid [13],SiO2-HClO4 [14],polymer-supported sulphonic acid [15], 4-(1-imidazolium) butane sulfonate (IBS) [16],ionic liquids [17, 18],heteropoly acid [19],strontium(II) triflate [20],PPA-SiO2 [21],NBS [22],NaHSO4 [23],Cu-exchanged heteropoly acids [24], NaHSO4.SiO2 [25],ferric hydrogensulfate [26],trityl chloride [27], nickel-doped SnO2 nanoparticles [28] and NiO-SnO2 composite nano-powder [29].

Metal phosphates glasses,such as barium phosphates,have been of large interest for a variety of technologies due to several exclusive properties such as high thermal expansion coefficient, low viscosity,UV transmission,or electrical conduction. Important biological applications for calcium phosphate glasses exist,also,as it was demonstrated that they are biocompatible as bones and dental implants [30, 31, 32, 33].

Despite this wide range of applications,the use of alkaline phosphates such as barium and calcium phosphates has not been receiving any attention in organic synthesis. This work is justified as a first work for the evaluation of the catalytic activity of barium phosphates.

Barium phosphate is known for its luminescence and was found to be a good host for rare earth-doped luminescent materials. Different methods have been reported for the preparation of barium phosphate including conventional solid-state reaction,sol- gel,simple precipitation,and hydrothermal method [34, 35, 36, 37]. However the solid-state method has disadvantages of poor particle distribution,high sintering temperature and long reaction time. Recently these problems have been improved by chemical synthetic methods which can be done at lower temperatures and have chemical homogeneity [38, 39]. In this paper a modified simple precipitation method is applied for the preparation of barium phosphate nanopowder.

Based on the above information and due to our interest in developing the synthetic methodologies for the construction of heterocyclic compounds [40, 41, 42, 43, 44, 45],herein,a detailed account of our focused attention toward construction of the 1-amidoalkyl-2- naphthol derivatives is reported,via the reaction of aldehydes, 2-naphthol and an amide (or urea) in high yields in the presence of Ba3(PO4)2 nanopowder as catalyst (Scheme 1).

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Scheme 1.Preparation of 1-amidoalkyl-2-naphthol derivatives.
2. Experimental 2.1. Reagents and instrumentation

All reagents were purchased from Merck and Aldrich and used without further purification. All yields refer to isolated products after purification. The NMR spectra were recorded on a Bruker Avance DPX 400 MHz instrument. The spectra were measured in DMSO-d6 relative to TMS (0.00 ppm). Elemental analysis was performed on a Heraeus CHN-O-Rapid analyzer. TLC was performed on silica gel Polygram SIL G/UV 254 plates. The powder X-ray diffraction patterns were measured with a Bruker D8 Advance diffractometer using Cu-Ka irradiation. FE-SEM was taken by a Hitachi S-4160 photograph to examine the shape and size of BaPO4 nano-particles. Dynamic light scattering (DLS) measurement was done using a Malvern Zetasizer Nano ZS (ZEN 3600) instrument.

2.2. Preparation of Ba3(PO4)2 nano-powder

To an aqueous solution of BaCl2 (10 mmol BaCl2 in 50 mL of water),NH4H2PO4 (10 mmol dissolved in 50 mL of EtOH/H2O (50/ 50) + triethyl ammonium chloride (15 mmol) + 5 mL NH4OH (aqueous solution 37%)) was added drop-wise with vigorous stirring at room temperature. After the dropping process was completed,the resultant mixture was aged for 30 min. The afforded precipitates were separated from the mother liquor by filtration and were washed with distilled water several times,then were dried at 100 ℃. The BaPO4 nano-particles were pulverized for analysis.

2.3. General procedure

To a mixture of aromatic aldehyde (1 mmol),2-naphthol/ dibenzofuran-2-ol (1 mmol) and acetamide/bezamide/urea (1.3 mmol) was added Ba3(PO4)2 nano-particles (0.1 mmol),and the mixture was heated at 100 ℃ in an oil bath for the appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction,mass was cooled to 25 ℃ and the mixture was dissolved in pure acetone. The catalyst was removed by simple filtration. The solvent was evaporated and the solid product was purified by recrystallization from ethanol.

N-((2-Hydroxynaphthalen-1-yl)(phenyl)methyl)-3-methylbenzamide: 1H NMR (400 MHz,DMSO-d6): δ 2.43 (s,3H),6.98 (d, 1H,J = 8.7 Hz),7.06-7.58 (m,11H),7.89-7.95 (m,3H),8.02 (d,1H, J = 8.3 Hz),9.47 (d,1H,J = 8.7 Hz,NH),10.37 (s,1H,OH); 13C NMR (100 MHz,DMSO-d6): δ 21.2,56.9,118.9,126.6,126.8,126.9, 127.6,127.9,128.3,128.6,128.7,128.9,129.2,130.6,130.9,131.1, 133.0,134.5,136.1,137.8,142.9,158.8,167.1; Calcd. for C25H21NO2: C,81.72; H,5.76; N,3.81,Found: C,81.85; H,5.89; N,3.93.

N-((4-Bromophenyl)(2-hydroxynaphthalen-1-yl)methyl)-3- methylbenzamide: 1H NMR (400 MHz,DMSO-d6): δ 2.44 (s,3H), 7.01-7.58 (m,11H),7.90-7.95 (m,3H),8.02 (d,1H,J = 8.4 Hz),9.14 (d,1H,J = 8.6 Hz,NH),10.31 (s,1H,OH); 13C NMR (100 MHz, DMSO-d6): δ 21.3,57.0,118.8,124.2,126.6,126.7,126.8,127.8, 128.3,128.6,128.7,129.2,130.5,130.9,131.2,131.7,132.9,134.4, 135.9,137.7,142.9,158.8,167.0; Calcd. for C25H20BrNO2: C,67.27; H,4.52; N,3.14,Found: C,67.41; H,4.69; N,3.31.

N-((2-Hydroxynaphthalen-1-yl)(3-nitrophenyl)methyl)-3- methylbenzamide: 1H NMR (400 MHz,DMSO-d6): δ 2.44 (s,3H), 7.01-7.59 (m,7H),7.90-7.97 (m,4H),8.02 (d,1H,J = 8.4 Hz),8.05 (s,1H),8.22 (d,1H,J = 8.0 Hz),9.17 (d,1H,J = 8.5 Hz,NH),10.39 (s, 1H,OH); 13C NMR (100 MHz,DMSO-d6): δ 21.2,57.0,118.9,124.7, 125.3,126.7,126.8 (2C),127.1,127.8,128.2,128.5 (2C),128.9, 130.5,130.9,131.2,132.9,134.5,135.8,137.7,139.6,145.3,158.8, 166.9; Calcd. for C25H20N2O4: C,72.80; H,4.89; N,6.79,Found: C, 72.97; H,5.06; N,6.94.

N-[(2-Hydroxydibenzofuran-1-yl)(phenyl)methyl)-3-methylbenzamide: 1H NMR (400 MHz,DMSO-d6): δ 2.43 (s,3H,CH3), 7.05-7.70 (m,13H),7.75 (d,1H,J = 8.1 Hz),7.90-7.94 (m,2H),8.76 (d,1H,J = 8.5 Hz,NH),9.94 (s,1H,OH); 13C NMR (100 MHz,DMSOd6): δ 21.2,57.0,111.9,112.4,119.8,119.9,122.7,122.9,124.6, 125.4,127.5 (2C),127.8,128.3,128.4,128.7,128.9,130.6,135.9, 137.7,142.7,153.9,1=.5,156.8,167.6; Calcd. for C27H21NO3: C, 79.59; H,5.19; N,3.44,Found: C,79.72; H,5.36; N,3.57.

N-[(2-Hydroxydibenzofuran-1-yl)(4-methylphenyl)methyl)-3- methylbenzamide: 1H NMR (400 MHz,DMSO-d6): δ 2.27 (s,3H, CH3),2.43 (s,3H,CH3),7.05 (d,1H,J = 8.6 Hz,CH),7.09 (d,2H, J = 7.9 Hz),7.11-7.35 (m,6H),7.45 (t,1H,J = 7.9 Hz),7.62 (d,1H, J = 8.0 Hz),7.70 (d,1H,J = 8.0 Hz),7.75 (d,1H,J = 8.3 Hz),7.91-7.96 (m,2H),8.79 (d,1H,J = 8.6 Hz,NH),10.02 (s,1H,OH); 13C NMR (100 MHz,DMSO-d6): δ 21.2,21.7,57.2,111.8,112.5,119.7,119.9, 122.7,123.0,124.7,125.5,127.6,127.8,128.0,128.5,128.7,129.8, 130.6,135.8,137.6,139.8,142.8,153.8,1=.6,157.1,167.0; Calcd. for C28H23NO3: C,79.79; H,5.50; N,3.32. Found: C,79.98; H,5.67; N,3.47.

N-[(2-Hydroxydibenzofuran-1-yl)(4-methoxyphenyl)methyl)- 3-methylbenzamide: 1H NMR (400 MHz,DMSO-d6): δ 2.42 (s,3H, CH3),3.77 (s,3H,OCH3),6.97 (d,2H,J = 7.9 Hz),7.03 (d,1H, J = 8.5 Hz,CH),7.11-7.36 (m,6H),7.44 (t,1H,J = 8.0 Hz),7.63 (d, 1H,J = 8.0 Hz),7.70 (d,1H,J = 8.0 Hz),7.75 (d,1H,J = 8.3 Hz),7.91- 7.96 (m,2H),8.74 (d,1H,J = 8.5 Hz,NH),10.05 (s,1H,OH); 13CNMR (100 MHz,DMSO-d6): δ 21.0,=.9,57.0,111.8,112.4,114.1,119.6, 119.9,122.5,122.9,124.6,125.3,127.4,127.7,128.5,128.7,130.6, 130.9,135.8,137.7,142.7,154.1,1=.6,156.9,160.6,167.1; Calcd. for C28H23NO4: C,76.87; H,5.30; N,3.20,Found: C,77.06; H,5.42; N,3.35.

N-[(2-Hydroxydibenzofuran-1-yl)(3-nitrophenyl)methyl)-3- methylbenzamide: 1H NMR (400 MHz,DMSO-d6): δ 2.43 (s,3H, CH3),7.08 (d,1H,J = 8.5 Hz,CH),7.14 (d,1H,J = 8.2 Hz),7.20 (t,1H, J = 8.0 Hz),7.27 (t,1H,J = 7.9 Hz),7.35 (d,1H,J = 7.8 Hz),7.43-7.46 (m,2H),7.63 (d,1H,J = 8.0 Hz),7.70 (d,1H,J = 7.9 Hz),7.75 (d,1H, J = 8.4 Hz),7.89-7.95 (m,3H),8.06 (s,1H),8.21 (d,1H,J = 7.9 Hz), 8.81 (d,1H,J = 8.5 Hz,NH),10.15 (s,1H,OH); 13C NMR (100 MHz, DMSO-d6): δ 21.2,57.6,111.9,112.6,119.7,119.9,122.6,122.9, 124.7,124.9,125.5,125.8,127.0,127.5,127.9,128.4,128.7,129.0, 130.8,135.8,137.7,139.8,145.3,153.8,1=.3,156.9,167.2; Calcd. for C27H20N2O5: C,71.67; H,4.46; N,6.19,Found: C,71.78; H,4.59; N,6.34.

N-[(2-Hydroxydibenzofuran-1-yl)(4-bromophenyl)methyl)-3- methylbenzamide: 1H NMR (400 MHz,DMSO-d6): δ 2.42 (s,3H, CH3),7.04 (d,1H,J = 8.6 Hz,CH),7.14 (d,1H,J = 8.3 Hz),7.18-7.37 (m,7H),7.44 (t,1H,J = 8.0 Hz),7.63 (d,1H,J = 7.9 Hz),7.69-7.75 (m,2H),7.89-7.93 (m,2H),8.79 (d,1H,J = 8.6 Hz,NH),9.96 (s,1H, OH); 13C NMR (100 MHz,DMSO-d6): δ 21.3,57.3,111.8,112.3, 119.6,119.9,122.5,122.9,124.5,124.9,125.4,127.6,127.7,128.6, 128.9,129.2,130.4,131.6,135.8,137.7,142.7,153.9,1=.4,156.9, 167.3; Calcd. for C27H20BrNO3: C,66.68; H,4.14; N,2.88,Found: C, 76.85; H,4.29; N,3.01.

N-[(2-Hydroxydibenzofuran-1-yl)(3-nitrophenyl)methyl)benzamide: 1H NMR (400 MHz,DMSO-d6): δ 7.07 (d,1H,J = 8.6 Hz,CH),7.14 (d,2H,J = 8.4 Hz),7.19-7.28 (m,2H),7.46 (d,1H, J = 7.9 Hz),7.51-7.64 (m,4H),7.69-7.76 (m,2H),7.87-7.92 (m, 3H),8.04 (s,1H),8.21 (d,1H,J = 7.9 Hz),8.86 (d,1H,J = 8.5 Hz,NH), 10.21 (s,1H,OH); 13C NMR (100 MHz,DMSO-d6): δ 57.5,111.8, 112.5,119.5,119.8,122.5,122.8,124.7,124.8,125.6,125.9,127.0, 127.6,127.9,128.6,128.7,129.1,135.2,139.5,145.4,153.8,1=.2, 156.8,167.0; Calcd. for C26H18N2O5: C,71.23; H,4.14; N,6.39, Found: C,71.41; H,4.39; N,6.47.

N-[(2-Hydroxydibenzofuran-1-yl)(4-bromophenyl)methyl)- benzamide: 1H NMR (400 MHz,DMSO-d6): δ 7.05 (d,1H,J = 8.5 Hz, CH),7.13 (d,1H,J = 8.2 Hz),7.18-7.41 (m,6H),7.52-7.75 (m,6H), 7.88 (d,2H,J = 7.8 Hz),8.65 (d,1H,J = 8.5 Hz,NH),9.84 (s,1H,OH); 13C NMR (100 MHz,DMSO-d6): δ 57.6,111.9,112.5,119.6,119.9, 122.5,122.9,124.3,124.7,125.4,127.4,127.8,128.8,128.9 (2C), 131.6,134.9,143.0,153.8,1=.7,156.9,167.2; Calcd. for C26H18BrNO3: C,66.11; H,3.84; N,2.97,Found: C,66.26; H, 3.95; N,3.11.

N-[(2-Hydroxydibenzofuran-1-yl)(4-bromophenyl)methyl)acetamide: 1H NMR (400 MHz,DMSO-d6): δ 2.01 (s,3H,CH3),6.91 (d,1H,J = 8.4 Hz,CH),7.13 (d,1H,J = 8.3 Hz),7.19 (t,1H,J = 7.9 Hz), 7.28 (t,1H,J = 7.9 Hz),7.35-7.41 (m,4H),7.63 (d,1H,J = 7.9 Hz), 7.70-7.75 (m,2H),8.24 (d,1H,J = 8.4 Hz,NH),9.14 (s,1H,OH); 13C NMR (100 MHz,DMSO-d6): δ 23.3,57.0,111.9,112.6,119.5,119.8, 122.5,122.7,124.3,124.8,125.6,127.7,128.9,131.7,142.8,153.9, 1=.7,156.9,169.4; Calcd. for C21H16BrNO3: C,61.48; H,3.93; N, 3.41,Found: C,61.66; H,4.11; N,3.59.

3. Results and discussion

In order to determine the crystalline structure and phase composition of the Ba3(PO4)2 nano-powder,X-ray diffraction (XRD) analysis using Cu-Ka radiation was applied (Fig. 1). The XRD pattern of Ba3(PO4)2 nano-powder exhibited diffraction pattern characteristics of the tetragonal structure with pronounced 18.32, 26.47,28.82,32.77,38.17,38.52,42.22,43.42,48.27,48.72,52.77 and 54.57 peaks (Fig. 1). The average crystallite diameter of the as prepared powder was determined by XRD,using the highest peak of the Ba3(PO4)2 phase,according to the Scherrer equation. The average crystalline size estimated at 80 nm.

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Fig. 1.XRD pattern of Ba3(PO4)2 nano-particles.

The average crystalline size of the Ba3(PO4)2 nano-powder was characterized by field emission scanning electron microscopy (FE-SEM). Fig. 2 shows the FE-SEM micrographs of the Ba3(PO4)2 nano-particles. Based on the FE-SEM observation,the Ba3(PO4)2 nano-particles contain spherical or ellipsoidal shapes. The particle sizes were mainly distributed in the range of 60-200 nm. The size of about 50 particles of Ba3(PO4)2 was measured and the average particle size was obtained as 85 nm.

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Fig. 2.FE-SEM micrographs of Ba3(PO4)2 nano-particles.

The dynamic light scattering (DLS) analysis was used to determine the particle size distribution of Ba3(PO4)2 nano-powder. Fig. 3 shows grain size distributions of Ba3(PO4)2 nano-powders. The powder milled for 2 h and sonicated in ethanol for 1 h had monomodal distributions with median particle size of 88 nm.

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Fig. 3.Particle size distribution of Ba3(PO4)2 nano-particles.

In order to introduce the application of Ba3(PO4)2 nanopowders in organic synthesis,the preparation of 1-amidoalkyl-2-naphthol derivatives was investigated,and as a preliminary test reaction, catalytic three-component reaction of bezaldehyde,2-naphthol and an acetamide in the presence of Ba3(PO4)2 nanopowder as a catalyst was examined (Scheme 1). Ba3(PO4)2 nanopowder exhibited high activity and the corresponding product was produced in high yield (Table 1). The use of bulk commercial Ba3(PO4)2 instead of Ba3(PO4)2 nanopowder in the test reaction gives the product in lower yield (72%) under the same reaction condition as solvent-free,catalyst (0.083 mmol),T = 100 ℃,time: 45 min. The higher surface area of Ba3(PO4)2 nanopowder is the reason for better catalytic activities than those of bulk material.

Table 1
Optimization of the reaction conditions.

To optimize the reaction conditions,the reaction was carried out using different solvents (Table 1,entries 2-7) or solvent-free condition (Table 1,entry 1). It was found that solvent-free is the best conditions of the reaction in terms of reaction times and yields (Table 1,entry 1). Polar solvents gave a low yield of product,but non-polar solvents did not affect the reaction,and no yield of product was obtained in non-polar media.

Secondly,the effect of temperature and catalyst amount on the reaction was investigated,and it was found that 0.1 mmol of Ba3(PO4)2 at 100 ℃ catalyzes the reaction smoothly with a high yield of product (Table 1,entry 13).

Finally,to understand the scope and limitation of this reaction, different aldehydes and ureas/amides were investigated (Table 2). The reaction of 2-naphthol,with various benzaldehydes containing electron donation and electron withdrawing groups and acetamide/ benzamide/urea was carried out in the presence of 0.1 mmol Ba3(PO4)2 nanopowders at 100 ℃ and a series of 1-amidoalkyl-2-naphthols were obtained in good to high yields (Table 2,entries 1-22). In all cases,benzaldehydes carrying either electron-donating or electron-withdrawing groups reacted successfully and gave the products in high yields. However,in the case of alkylaldehydes,complicated products were formed under the similar conditions,which probably resulted from the aldol formation (Table 2,entry 22). The use of cyclohexanecarbaldehyde did not correspond to the expected product (Table 2,entry 23). Based on the obtained results,the electronic effects and the steric effects of the substituents played significant roles in the yields of products. Aromatic aldehyde systems that possessed substitutions at the ortho,meta,or para positions afforded products,however, aromatic aldehydes containing electron-withdrawing groups gave higher yields than those with electron-donating groups.

Table 2
Preparation of 1-amidoalkyl-2-naphthol derivatives using Ba3(PO4)2 as catalyst (0.083 mmol, 100 ℃).

Encouraged by the results obtained with 2-naphthol,we extended this protocol to the one-pot,three-component reaction of aromatic aldehyde,amides,and 2-hydroxydibenzofuran using the above reaction condition optimized for 2-naphthol. The reactions with various aromatic aldehydes bearing electrondonating and electron-withdrawing groups and amides gave product in excellent yields (Table 3).

Table 3
Preparation of amidoalkyl dibenzofuranol derivatives using Ba3(PO4)2 as catalyst (0.083 mmol, 100 ℃).

The use of 1-naphthol instead of 2-naphthol resulted in a complex mixture of products that cannot be separated easily from the reaction mixture. Thus 1-naphthol is not found to be a suitable starting material.

On the basis of obtained results as well as literature surveys [4- 29],a plausible mechanism was portrayed for the synthesis of 1- amidoalkyl-2-naphthol derivatives (Scheme 2). At first the electrophilic center of aldehyde is more activated by the interaction of oxygen nucleophile with barium phosphate which facilitates nucleophilic attachment of 2-naphthol to form intermediate A,which continues via water elimination to ortho-quinone methides (B). Activation of this intermediate by barium phosphate catalyst following by the Michael addition of the amide group leads to the formation of targeted molecules (Scheme 2).

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Scheme 2.A plausible mechanism for the synthesis of 1-amidoalkyl-2-naphthol derivatives.

Finally,the crude product was dissolved in pure acetone and centrifuged to recover the catalyst by filtration (10 nm filter papers),which was followed by washing several times with acetone,drying at 100 ℃ for 1 h,and reuse without significant loss of catalyst activity (five runs were examined). The results of catalyst recovery are summarized in Fig. 4.

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Fig. 4.Catalyst recovery based on the reaction of 2-naphthol/benzaldehyde/ acetamide.
4. Conclusion

The nanopowder Ba3(PO4)2,prepared by a simple precipitation method,was used as an efficient catalyst for the preparation of 1- amidoalkyl-2-naphthol derivatives. It was stated that the use of 0.083 mmol of Ba3(PO4)2 as catalyst for the catalytic condensation reaction of aromatic aldehydes,2-naphthol and amides/urea under ambient condition provides high yields of products. Certainly,the simplicity of the accommodated catalytic system makes it suitable for further research and practical applications.

Acknowledgments

We are thankful to the Najafabad Branch,Islamic Azad University Research Council for partial support of this research

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Preparation of 1-amidoalkyl-2-naphthol derivatives using barium phosphate nano-powders
Hadi Taghrir, Majid Ghashang , Mohammad Najafi Biregan