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Journal of the Chilean Chemical Society

On-line version ISSN 0717-9707

J. Chil. Chem. Soc. vol.61 no.3 Concepción Sept. 2016 





1 Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
Center of Basic Researches in Infectious Diseases and Department of Medical Mycology and Parasitology School of Medicine, Shiraz University of Medical Sciences, Post code 71348-45794, Shiraz, Iran
Department of Chemistry, College of Science, Yazd University, Yazd, PO Box 8915813149, I. R. Iran
* e-mails:


Nano-TiCl4.SiO2 has been introduced to be an extremely efficient catalyst for the preparation of N,N'-alkylidene bisamides from various aldehydes and amides under mild conditions. We synthesized this solid Lewis acid catalyst by the reaction of nano-SiO2 and TiCl4. The processor was simple and environmentally benign with high to excellent yields. Our method has the advantages of high yields, simple methodology, and easy work-up. The antimicrobial and antifungal activities of some of the synthetic compounds were determined by broth microdilution methods as recommended by Clinical Laboratory Standard Institute. Further studies still needed to investigate the other biological activities of the compounds.

Keywords: Nano-TiCl4.SiO2 Heterogeneous catalyst, N,N'-Alkylidene bisamides, Antifungal, Antibacterial.



Amide and bisamide compounds are main part of many peptidomimetic1 and they play a major role in the expansion and composition of biological and pharmacological systems. They are of considerable interest in the synthesis of pharmacological materials such as peptidomimetic compounds2,3 and gem-diaminoalkyl residues in retro-inverso pseudopeptide derivatives4 by treating the corresponding amide with iodobenzene bistrifluoroacetate.5 Generally symmetrical alkylidene bisamides are synthesized by the direct reaction of aldehydes with the corresponding amides under suitable catalytic condition. In this topic, let us examine the various conditions of the catalysts such as sulfuric acid6, sulfonic acid7, triflic acid8, p-toluene sulfonic acid9, SiO2-MgCl210, hydrochloric acid11, CC- or DCMT activatd DMSO12, phosphotungstic acid13, boric acid 14, silica coated magnetic NiFe2O4 nanoparticle supported polyphosphoric acid15 and p-toluenesulfonic acid.16 Our studies towards the development of more efficient methods accompanied with higher yields for the synthesis of N,N'-Alkylidene bisamides in the presence of nano-TiCl4.SiO2. In addition, the antimicrobial and antifungal activities of some of the synthetic compounds were evaluated by broth microdilution methods.


The chemicals were purchased from Merck Company and used without any additional purification. The products were characterized by FT-IR (ATR), 1H-NMR, and a comparison of their physical properties with those reported in the literature. FT-IR (ATR) spectra were run on a Bruker, Eqinox 55 spectrometer. A Bruker (DRX-400 Avance) NMR was used to record the 1H NMR spectra. Spectrophotometer (Company BAUSCH & LOMB, US), Vortex mixer (Company Lab net), Tween 20 (Company Roche, Germany).

General experimental procedure for the synthesis of N,N′-alkylidene bisamide

A mixture of aldehyde (1 mmol), amide (2 mmol), n-hexane (5 ml) and nano-TiCl4.SiO2 (0.04 g) was refluxed for appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and filtered. The catalyst was separated from the reaction mixture by boiling ethanol. The crude solid product was purified by recrystallization procedure in ethanol:water, 80:20.

Biological study


The antifungal activities of the synthetic compounds against some American Type Culture Collection (ATCC) strains of fungi, including Candida albicans (ATCC 10261), Candida tropicalis (ATCC 750), Candida krusei (ATCC 6258), Candida glabarata (ATCC 90030), Candida dubliniensis (CBS 8501), Aspergillus flavus (ATCC 64025), and Aspergillus fumigatus (ATCC 14110) as well as two clinical isolates of yeasts identified by PCR-RFLP were determined. The susceptibility of all clinical isolates of fungi against selected antibiotics was examined by microdilution and disk diffusion methods The antibacterial activities of the above compounds against standard species of Staphylococcus aureus (ATCC 25923), Enterococcus faecalis (ATCC 11700), Escherichia coli (ATCC 25922) and Pseudomonas aeruginosa (ATCC 27853) were also determined in this study. The susceptibility of all clinical isolates of fungi against select compounds was examined by microdilution and disk diffusion methods.17,18

Determination of minimum inhibitory concentration

MICs were determined using the broth microdilution method recommended by the CLSI with some modifications.17,18 Briefly, for determination of antimicrobial activities against fungi, serial dilutions of the synthetic compounds (1-1024 μg/mL) were prepared in 96-well microtiter plates using RPMI-1640 media (Sigma, St. Louis, MO, USA) buffered with MOPS (Sigma). Stock inoculums were prepared by suspending three colonies of the examined yeast in 5 mL sterile 0.85% NaCl, and adjusting the turbidity of the inoculums to 0.5 McFarland standards at 530 nm wavelengths (this yields stock suspension of 1-5 × 106 cells/mL). For moulds (Aspergillus spp. and dermatophytes), conidia were recovered from the 7-day old cultures grown on potato dextrose agar by a wetting loop with tween-20. The collected conidia were transferred in sterile saline and their turbidity was adjusted to OD=0.09-0.11 that yields 0.4-5 × 106 conidia/mL. Working suspension was prepared by making a 1/50 and 1/1000 dilution with RPMI of the stock suspension for moulds and yeasts, respectively. Working inoculums (0.1 mL) were added to the microtiter plates, which were incubated in a humid atmosphere at 30°C for 24—48 h. Uninoculated medium (200 μL) was included as a sterility control (blank). In addition, growth controls (medium with inoculums but without antibiotics or the synthetic compounds) were also included. The growth in each well was compared with that of the growth in the control well.


TiCl4.SiO219-26 is an efficient and reusable acidic catalyst. This catalyst is synthesized via reaction of nano-silica gel with TiCl4 in chloroform at room temperature. In continue of our investigations on solid acid application in organic synthesis, we tried to develop new synthetic method to prepare N,N'-alkylidene bisamides and find the best reaction conditions. The reaction of benzamide and benzaldehyde was examined under various conditions and different quantities of TiCl4.SiO2 and nano-TiCl4.SiO2 (Table 1). According to our results, the best condition is the reaction in solvent free condition using 0.1 g of TiCl4.SiO2 or 0.04 g of nano-TiCl4.SiO2. The results showed an improved reaction rate and yield (Table 1, Entries 2, 11).


Table 1. Synthesis of N, N'-(4-nitrophenylmethylene) dibenzamide
under various conditions

a Isolated yield.
b Using mixer mill (MM 400) in 25 Hz frequency.
c Using BANDELIN Sonopulse HD 3200 ultrasonic apparatus with
power equal to 20 KHz.
d Using microwave oven Kenwood, 1300W


Once the scope of the reaction condition was established, the reusability of catalyst was examined. After performing the reaction, the catalyst was separated, washed with acetone, dried and re-used up to 3 times in reaction without losing its activity (Figure 1).


Fig. 1. Reusability of nano-TiCl4.SiO2 catalyst.


Next, the scale of this procedure was explored using a wide range of aldehydes containing electron-donating or electron-withdrawing groups attaching to aromatic ring (Table 2).


Table 2. Preparation of N,N'-alkylidene bisamide derivatives in
the presence of nano-TiCl4.SiO2a

a Reaction conditions: amide (2 mmol), aldehyde (1 mmol),
nano-TiCl4. SiO2 (0.04 g).
b Isolated yield.


In all cases, aromatic aldehydes containing electron-withdrawing groups gave higher yield of products in shorter time than aromatic aldehydes containing electron-withdrawing groups (Table 2, entries 3 and 9). In methyl carbamate, the nucleophilicity of nitrogen is higher than acetamide. Thus, methyl carbamates produce a good yield of product in shorter time than acetamides (Table 2, entries 4).

This protocol is effective special for primary amides but secondary amides or primary sulfonamides (Scheme 1and 2).


Scheme 1. The selectivity of protocol for primary amides versus secondary amides


Scheme 2. The selectivity of protocol for primary amides versus sulfonamides


Nano-TiCl4.SiO2 catalyzes the reaction of benzaldehyde with urea to produce corresponding bisamides and imines with different yields (Scheme 3).


Scheme 3. Reaction of benzaldehyde with urea


N,N,N',N'-(1, 5-pentylene)tetrabenzamide was also produced via the reaction of 1 mmol of glutardialdehyde with 4 mmol of benzamide in the presence of Nano-TiCl4.SiO2 (Scheme 4).


Scheme 4. Synthesis of N,N,N',N'-(1, 5-pentylene)tetrabenzamide from
glutardialdehyde and benzamide


N,N’-(methylene)dibenzamide was produced via the reaction of 1, 3, 5-trioxane with benzamide in the presence of nano-TiCl4.SiO2 (Scheme 5).


Scheme 5. Synthesis of N,N’-(methylene)dibenzamide from 1, 3,
5-trioxane with benzamide


The chemo-selectivity of bisamide preparation was examined via reaction of 4-nitrobenzaldehyde with benzamide and acetamide in one vessel in the presence of nano-TiCl4.SiO2. The preparation of mixed products approves no chemo selectivity between aromatic and aliphatic amides. Reaction of benzamide with 3-phenylpropione aldehyde and benzaldehyde in one vessel and producing a mixture of corresponding bisamides show no chemo selectivity between aromatic and aliphatic aldehydes. Previously, two types of mechanisms were reported for bisamide formation from aldehyde and amide.13,14

According to our knowledge, we have proposed a mechanism for formation of bisamides in the presence of nano-TiCl4.SiO2 (Scheme 6).


Scheme 6. The suggested mechanism for bisamide formation from aldehyde and amide


None of the selected compounds exhibited antifungal activity against the examined fungi at the tested concentrations (Table 3). Moreover, the examined compounds failed to inhibit the growth of the Gram-positive and gram-negative bacteria at the concentration up to and including 256μg/mL (Table 4). Further studies still needed to investigate other biological activities of these compounds.


Table 3. Minimum inhibitory and fungicidal concentrations of the synthetic compounds ^g/mL)
against the examined fungi.


Table 4. MIC and MFC ^g/mL) values for the synthetic compounds against bacteria.



N,N'-(phenylmethylene)dibenzamide (Table 2, B1)

FT-IR: (ATR, neat, cm-1): 3275 (N-H stretch), 1650 (C=O stretch), 1480 (N-H bend), 715, 799 (C-H bend); 1H NMR (DMSO-d6, ppm): δ 9.01 (d, J=7.7 Hz, 2H, N-H),7.92 (d, J=7.8 Hz, 4H),7.56 (t, J=7.09 Hz, 2H),7.49 (t, J=7.5 Hz, 6H),7.39 (t, J=7.5 Hz, 2H),7.32 (t, J=7.07 Hz, 1H), 7.05 (t, J=7.72 Hz, 1H, CH).

Elemental analysis. Found, %: C 76.55; H 5.38; N 8.38. C21H18N2O2. Calculated, %: C 76.34; H 5.49; N 8.48.

N,N'-(3-nitrophenylmethylene)diacrylamide (Table 2, B2):

FT-IR: (ATR, neat, cm-1): 3242 (N-H stretch), 1664 (C=O stretch), 1628 (C=C stretch), 1346, 1528 (N=O stretch), 1520 (N-H bend), 966, 703, 667 (C-H bend); 1H NMR (DMSO-d6, ppm): δ 9.22 (d, J=7.4 Hz, 2H, N-H), 8.20 (d, J=1.74 Hz, 2H), 7.82 (d, J=7.78 Hz, 1H), 7.70 (t, J=8.03 Hz, 1H), 6.74 (t, J=7.49 Hz, 1H, CH), 6.35 (dd, J=17.09 Hz, 10.19, 2H), 6.17 (dd, J=17.10 Hz, 1.73, 2H), 5.68 (dd, J =10.17 Hz, 1.78, 2H). Elemental analysis. Found, %: C 56.56; H 4.58; N 15.38. C13H13N3O4. Calculated, %: C 56.72; H 4.76; N 15.27.

N,N'-(4-nitrophenylmethylene)dibenzamide (Table 2, B3):

FT-IR: (ATR, neat, cm-1): 3256 (N-H stretch), 1649 (C=O stretch), 1343, 1507 (N=O stretch), 1546 (N-H bend), 852 (C-H bend); 1HNMR (DMSO-d6, ppm): δ 9.2 (d, J=5.0 Hz, 2H, N-H), 8.26(d, J=6.9 Hz, 2H), 7.93(d, J=5.6 Hz, 4H), 7.75(d, J=6.9 Hz, 2H), 7.58(s, 2H), 7.50(m, 4H), 7.09 (brs, 1H, CH).13C-NMR (DMSO-d6, ppm): 166.7, 134.41, 132.62, 129.21, 128.91, 128.47, 124.38. Elemental analysis, Found, %: C 66.99; H 4.78; N 11.15. C21H17N3O4. Calculated, %: C 67.19; H 4.56; N 11.19.

N,N'-(4-nitrophenylmethylene)dimethylcarboxamide (Table 2, B4):

FT-IR: (ATR, neat, cm-1): 3306 (N-H stretch), 1706 (C=O stretch), 1600 (C=C stretch), 1349, 1530 (N=O stretch), 1550 (N-H bend), 1251, 1195 (C-O stretch), 871 (C-H bend); 1H NMR (DMSO-d6, ppm): δ 8.2(d, J=7.5 Hz, 2H), 8.1 (brs, 2H, N-H), 7.6(d, J=7.6 Hz, 2H), 6.24(brs, 1H, CH), 3.58 (s, 6H, OMe); 13C-NMR (DMSO-d6, ppm): 156.6, 148.1, 147.9, 128.7, 124.3, 61.9, 52.5. Elemental analysis, Found, %: C 46.50; H 4.70; N 14.90. C11H13N3O6. Calculated, %: C 46.65; H 4.63; N 14.84.

N,N'-(2,4-dichlorophenylmethylene)dimethylcarboxamide (Table 2, B5):

FT-IR: (ATR, neat, cm-1): 3309 (N-H stretch), 1708 (C=O stretch), 1550 (N-H bend), 720, 699 (C-H bend), 643 (C-Cl stretch); 1H NMR (DMSO-d6, ppm): δ 8.04 (sbr, 2H, N-H), 7.61 (d, J=2 Hz, 1H), 7.57 (d, J=8.45 Hz, 1H), 6.24 (dd, J=8.42 Hz, 1.9, 1H), 6.24(t, J=7.55 Hz, 1H, CH), 3.55(s, 6H, OMe); 13C-NMR (DMSO-4-, ppm): 156.3, 137.5, 134.1, 133.8, 130.3, 129.5, 128.1, 59.8, 52.4. Elementa6l analysis, Found, %: C 42.92; H 3.90; N 9.08; Cl 23.02. C11H12N2O4Cl2. Calculated, %: C 43.02; H 3.94; N 9.12; Cl 23.09.

N,N'-(3-nitrophenylmethylene)dibenzamide (Table 2, B6):

FT-IR: (ATR, neat, cm-1): 3250 (N-H stretch), 1646 (C=O stretch),1340 (N-H bend), 1339, 1533 (N=O stretch), 1505 (C=C stretch), 715, 695 (C-H bend);1H NMR (DMSO-d6, ppm): δ 9.2 (d, J=7.4 Hz, 2H, N-H), 8.35 (sbr, 1 H), 8.2 (dd, J=6.9 Hz, 1.37, 1H), 7.96(s, IH), 7.93(d, J=8.4 Hz, 4H), 7.71(t, J=7.9 Hz, 1 H), 7.58(t, J=7.2 Hz, 2H), 7.5(t, J=7.8 Hz, 4H), 7.09 (t, J=7.3 Hz, 1H, CH). Elemental analysis, Found, %: C 66.89; H 4.67; N 11.39. C21H17N3O4. Calculated, %: C 67.19; H 4.56; N 11.19.

N,N'-(2,4-dichlorophenylmethylene)diacetamide (Table 2, B7):

FT-IR: (ATR, neat, cm-1): 3285 (N-H stretch), 1665 (C=O stretch), 1425 (C=C stretch), 1518 (N-H bend), 856, 749 (C-H bend), 643 (C-Cl stretch); 1H NMR (DMSO-d6, ppm): δ 8.54 (d, J=7.19 Hz, 2H, N-H), 7.62 (d, .7=1.6 Hz, 1H), 7.5 (m, 2H), 6.6 (t, 7=7.55 Hz, 1H, CH), 1.84(s, 6H, CH3). Elemental analysis, Found, %: C 47.90; H 4.48; N 10.08; Cl 25.62. C11H12N2O2Cl2. Calculated, %: C 48.02; H 4.40; N 10.18; Cl 25.77.

N,N'-(1-butylene)dibenzamide (Table 2, B8):

FT-IR: (ATR, neat, cm-1): 3232 (N-H stretch), 1643 (C=O stretch), 1484, 1600 (C=C stretch), 1530 (N-H bend); 1H NMR (DMSO-d6, ppm): δ 8.52 (d, 7=7.62 Hz, 2H, N-H), 7.86 (d, 7=7.12 Hz, 4H), 7.55 (t, 7=7.12 Hz, 2H), 7.47(t, 7=7.7 Hz, 4H), 5.85(m, 1H, CH), 1.85 (td, 7=7.65 Hz, 7.42, 2H, CH2), 1.37(m, 2H, CH2), 0.938(t, 7=7.33 Hz, 3H, CH3). Elemental analysis, Found, %: C 73.09; H 6.57; N 9.39. C18H20N2O2. Calculated, %: C 72.95; H 6.80; N 9.45.

N,N'-(3-nitrophenyl-methylene)dimethylcarboxamide (Table 2, B9):

FT-IR: (ATR, neat, cm-1): 3287 (N-H stretch), 1701 (C=O stretch), 1515, 1343 (N=O stretch), 1556 (N-H bend), 1255, 1032(C-O stretch), 674, 783, 809 (C-H bend); 1H NMR (DMSO-d6, ppm): δ 8.24(s, 1H), 8.17 (d, 7=8.3 Hz, 1H), 8.15( sbr, 2H, NH), 7.82 (d, 7=7.6 Hz, 1H), 7.67 (t, 7=7.9 Hz, 1H), 6.25 (t, 7=7.9 Hz, 1H, CH), 3.61(s, 6H, OMe). Elemental analysis, Found, %: C 46.82; H 4.56; N 14.28. C11H13N3O6. Calculated, %: C 46.65; H 4.63; N 14.84.

N,N'-(3-phenyl-propylene)dibenzamide (Table 2, B10):

FT-IR: (ATR, neat, cm-1): 3299 (N-H stretch), 1637 (C=O stretch), 1508, 1579 (C=C stretch), 1545 (N-H bend), 690, 756 (C-H bend); 1H NMR (DMSO-d6, ppm): δ 8.64 (d, 7=7.5 Hz, 2H, N-H), 7.88 (d, 7=7.22 Hz, 4H), 7.54(t, 7=7.31 Hz, 2H), 7.48 (t, 7=7.69 Hz, 4H), 7.28 (m, 4H), 7.17 (m, 1H), 5.85 (m, 1H, CH), 2.69 (t, 7=8.15 Hz, 2H, CH2), 2.17 (dd, 7=15.4 and 7.31 Hz, 2H, CH2). Elemental analysis, Found, %: C 76.89; H 6.24; N 7.95. C23H22N2O2. Calculated, %: C 77.07; H 6.19; N 7.82.

N,N'-(3-phenyl-2-ene-propylene)dibenzamide (Table 2, B11):

FT-IR: (ATR, neat, cm-1): 3274(N-H stretch), 1647 (C=O stretch), 1484,1504 (C=C stretch), 1543 (N-H bend), 690, 756 (C-H bend); 1H NMR (DMSO-d6, ppm): δ 8.87 (d, 7=6.8 Hz, 2H, N-H), 7.92 (d, 7=7.36 Hz, 4H), 7.86 (t, 7=7.92 Hz, 2H), 7.56 (t, J=7.2 Hz, 2H), 7.48 (m, 4H), 7.35 (m, 2H), 7.28 (t, 7=7.32 Hz, 1H), 6.69 (d, 7=14.7 Hz, 1H, CH), 6.65 (m, 2H). Elemental analysis, Found, %: C 77.99; H 5.37; N 7.59. C23H20N2O2. Calculated, %: C 77.51; H 5.66; N 7.86.

N,N'-(2-hydroxyphenyl-methylene)dibenzamide (Table 2, B12):

FT-IR: (ATR, neat, cm-1): 3406-3268(O-H and N-H stretch), 1639 (C=O stretch), 1425 (C=C stretch), 1126 (C-N bend), 758 (C-H bend);1H NMR (DMSO-d6, ppm): δ 9.02 (d, 7=7.39 Hz, 2H, N-H), 8.03 (d, 7=7.27 Hz, 2H), 7.81(d, 7=7.31 Hz, 3H), 7.69 (m, 1H), 7.52 (m, 3H), 7.45 (m, 5H), 7.35 (m, 1H), 7.26 (t, 7=7.34 Hz, 1H, CH). Elemental analysis, Found, %: C 72.99; H 5.17; N 7.99. C21H18N2O3. Calculated, %: C 72.82; H 5.24; N 8.09.

N,N'-(methylene)dibenzamide (Scheme 5):

FT-IR: (ATR, neat, cm-1): 3308 (N-H stretch), 1634 (C=O stretch), 1487, 1578 (C=C stretch), 1526 (N-H bend), 1448 (CH2 bend); 1HNMR (DMSO-d6, ppm): δ 9.03 (t, 7=5.5 Hz, 2H, N-H), 7.9 (d, 7=7.14 Hz, 4H), 7.55 (t, 7=7.15 Hz, 2H), 7.48(t, 7=7.14 Hz, 4H), 4.84(t, 7=5.5 Hz, 2H, CH2). Elemental analysis, Found, %: C 69.99; H 4.97; N 11.48. C15H14N2O2. Calculated, %: C 70.85; H 5.55; N 11.02.


We have demonstrated simple methods for the synthesis of preparation of N,N′-alkylidene bisamides with using nano-TiCl4.SiO2 as eco-friendly and efficient catalyst in a one-pot procedure that has been developed. Short reaction times, high yields, a clean process, simple methodology, easy work-up and green conditions are advantages of this protocol. Even at this time our compounds didn't show antifungal and antibacterial activity but we suppose these negative results probably related to undesirable pharmacokinetic properties. Maybe some structural modifications could improve the pharmacokinetic properties of our compounds. We hope in future studies we could be able to synthe-size some effective derivatives of bisamides with different biological activities.


The Research Council of Yazd University is gratefully acknowledged for the financial support of design and synthesis of compounds. The antifungal activities of the synthetic compounds were evaluated in Shiraz University of Medical Sciences.



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