Syntheses of 5-substituted tetrazole derivatives have been reported by one-pot three-component reaction of various aldehydes (aryl, aryl with fused ring, aryl with extended conjugation, heterocyclic and aliphatic), hydroxylamine hydrochloride and sodium azide in the presence of potent, reusable, low cost and thermally stable catalyst, Ni-complex MCM-41 under conventional heating / microwave irradiation. The prepared materials were characterized by FT-IR, PXRD analysis, N2 adsorption and desorption, EDX, SEM and TEM microscopy, ICP-OES and TGA. The effect of solvent, temperature, catalyst loading and time for the syntheses of tetrazoles were optimized. The efficiency of Ni-MCM-41 catalyst is compared and discussed against the literature reports. The catalyst can be successively recovered by simple filtration method and reused upto five times with excellent yields upto 94%. In general, microwave irradiation technique gave better yields when compared to conventional heating irrespective of the nature of the substrate and their substituents.
Research Article
A green one pot three component synthesis of tetrazole under microwave irradiation using Ni Schiff base complex of mixed ligands on MCM-41 as an efficient heterogeneous catalyst
https://doi.org/10.21203/rs.3.rs-1648933/v1
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5-substituted tetrazoles
aldehyde
Ni-complex
MCM-41
heterogeneous catalyst
microwave irradiation
Tetrazoles are receiving much heed due to their prominent role in many fields of science viz., (i) In coordination chemistry as a ligand in the synthesis of imidoylazides [1] (ii) In the material applications including propellants [2], explosives [3], photoimaging stabilizers [4] (iii) In agriculture field herbicides [5] fungicides [6] (iv) In drugs as bio-isosteric replacement of carboxylic acid [7] and in the inhibition of HIV-1 reverse transcriptase [8] (Fig. 1). In addition, they possess anti-microbial activities, such as antibiotic [9], anti-allergic [10], antihypertensive [11], antidiabetic [12], anticonvulsant, antiulcer, antitubercular [13–15] and antagonists [16].
The most important class of tetrazole, 5-substituted-1H-tetrazole, can be synthesized mainly from the common strategy of reacting nitriles and azides [17, 18]. In this case, the nitrile substrate needs the presence of strong electron withdrawing group and high reaction temperature, which limits the scope of the reaction. Apart from that, these 5-substituted tetrazoles have also been described from the reaction of oxime with sodium azide [19] and from the reaction of cyanoacetamides with sodium azide [20].
In the past few years, researchers have been much curious about the synthesis of 5-substituted 1H-tetrazoles using aldehyde with hydroxylamine hydrochloride or oximes and NaN3 because of more availability and less toxicity of aldehydes compare to nitriles. Heravi et al have synthesized 5-substituted 1H-tetrazoles via the reaction of aldehydes, hydroxylamine and [bmim]N3 in DMF at 120 oC using Cu (OAc)2 catalyst [21]. Somayeh Behrouz has reported a nano catalyst, Cu2O using a similar type of reaction from aldehydes, hydroxylamine and TBAA in DMF at 100 oC [22]. Alibeik et al have described this type of reaction from aldehydes, hydroxylamine and NaN3 in DMF at 140 oC in the presence of a Cu-MCM-41 catalyst [23].
Many homogeneous and heterogeneous catalysts have been used for the synthesis of 5-substituted-1H-tetrazole derivatives such as Zn (OTf)2 [24], Cu2(OTf)2 [25], Fe (OAc)2 [26], BF3.OEt2 [27], AlCl3 [28], AgNO3 [29], Zn/Al hydrotalcite [30], COY zeolites [31], nano-ZnO/Co3O4 [32], Cu2O [33], ZnO [34], Amberlyst-15 [35], clay and modified clays [36]. However, many of these reported methods suffer from some snags like the use of toxic reagents, low yield, corrosive and fairly expensive metals as catalysts with harsh reaction conditions, longer reaction times etc. For these reasons, the design of benign and eco-friendly protocols for the synthesis of tetrazoles from easier and more available precursors is still highly desirable.
By considering greener strategy, firstly we have chosen heterogeneous catalysis over homogeneous, the simplistic separation of catalyst from reaction media and reused it for several times [37]. There are numerous ways to fix catalysts into heterogeneous supports, viz., grafting onto zeolites, co-polymerization, organic polymer and silica [38]. The mesoporous materials based on MCM-41 has unique properties like high thermal stability, high surface area, high pore volume, tunable pore size, controlled morphology and rich silanol groups in the inner walls of the MCM-41 [39–43].
Secondly, multi component reactions stand along with greener path, due to the atom economy, simple synthetic procedures and easy accessibility of wide range of substrates for the syntheses of complex organic compounds. As third, microwave irradiation technique is eco friendlier due to the less amount of time and energy consumption for carrying out the reaction.
Herein, we report the preparation and characterization of a heterogeneous catalyst, Ni-MCM-41 and its catalytic activity in the one pot three component synthesis of 5-substituted 1H-tetrazoles with a variety of aldehydes, hydroxylamine and sodium azide under microwave irradiation.
2.1 Materials and instruments
Tetraethylorthosilicate (TEOS), 3-aminopropyltrimethoxysilane (3APTMS), cetyltrimethylammoniumbromide (CTAB), 1,10-phenanthroline, 4-hydroxy-3-methoxybenzaldehyde (vanillin), nickel (II) acetatetetrahydrate, aromatic aldehydes, hydroxylamine hydrochloride, sodium azide and solvents were purchased from Sigma Aldrich, Molychem, Nice and Merck companies and used as received. IR spectra of prepared samples were recorded on an Avatar 370 model FT-IR spectrometer with KBr pellets. PXRD data were obtained from a Bruker D8 Advance powder X-ray diffractometer. The SEM/EDX micrographs were acquired from the JEOL model JSM 6390LV microscope. HR-TEM analysis was carried out on a JEOL JEM 2100 model. BET analysis was carried out using chemisorb 2750 TPD/TPR instrument. ICP-OES was used to find out the Ni-content in the sample. The TGA micrograph was recorded on a Q 500 Hi-Res instrument from 0-900 oC. A convection microwave oven (MC2846SL, LG 28L) was used to do the catalytic reactions. NMR spectra were recorded using a Bruker Avances III HD Nanobay 400 MHz model spectrometer. The chemical resonances (δ) were reported in parts per million (ppm). The MCM-41 material was concocted according to lucid literature [44].
2.2 Synthesis of Ni-MCM-41
A stirred methanolic solution of 3-APTMS (1 mmol) with vanillin (1 mmol) was refluxed for 3 h. Then a concentrated methanolic solution of Ni(OAc)2.4H2O (1 mmol) and 1,10 phenanthroline, (1 mmol) was poured into the reaction mixture with vigorous stirring for 3 h to follow the overhead conditions. After ceasing the reaction, the reaction mixture was dried using a rotary evaporator. The obtained crude Ni-complex was washed with methanol to get rid of the un-reactants and impurities. Afterwards, 1 g of calcinated MCM-41 was added to the above complex (0.6 g) over toluene and stirred for 24 h under N2 atmosphere at room temperature. Subsequently, the heterogeneous catalyst, Ni-MCM-41 (2.2 g) was recovered by a rotary evaporator (Scheme 1).
2.3 Synthesis of 5- substituted 1H-tetrazoles by using the heterogeneous catalyst Ni-MCM-41
2.3.1 Conventional method
A mixture of substituted aldehyde (1 mmol), NH2OH.HCl (1 mmol), NaN3 (1 mmol) and catalyst (40 mg) in 5 ml of DMF was heated at 120 o C for 6 h. Later on, the completion of the reaction was scrutinized by TLC (hexane/ethyl acetate (7:3)) and the Ni-MCM-41 catalyst was recovered by filtration. The filtrate was evaporated, followed by dissolution in water (5 mL) and acidified with 37% of HCl to obtain the solid product. Then the solid 5-substituted tetrazole was filtered, dried (Scheme 2) and confirmed by 1H-NMR spectra.
2.3.2 Microwave irradiation method
40 mg of the catalyst with a substituted aldehyde (1 mmol), NH2OH.HCl (1 mmol) and NaN3 (1 mmol) in 5 ml of DMF are placed in a vial and the mixture was subjected to microwave irradiation at 120°C for 30 min. The reaction was examined by TLC and the catalyst was discharged by filtration. Further, the filtrate was processed in a similar way as in the conventional method.
3.1 FT-IR spectroscopy
FT-IR spectra of the synthesized MCM-41and ligand have been discussed in the previous work [44]. The IR spectrum of Ni-complex and Ni-MCM-41 are shown in Fig. 2. It shows a peak around 1510 cm− 1 due to aromatic C = C stretching frequency in vanillin. The band due to C = N at 1647 cm− 1 in the ligand is shifted to 1594 cm− 1 in the nickel complex, indicating the participation of imine nitrogen in the complexation with nickel. When comparing the IR spectra of the ligand and complex, the -OCH3 stretching at 2938 cm− 1 is shifted to 2928 cm− 1. It reveals the participation of methoxy oxygen rather than phenolic oxygen upon the complexation. The C-H out of plane bending vibration of phenanthroline at 828 cm− 1 is shifted to 806 cm− 1 that indicates the coordination of phenanthroline nitrogen with the metal ion upon complexation [45]. In addition, the bands about 627 cm− 1 and 458 cm− 1 were correspond to vibration of Ni-N and Ni-O respectively, which confirmed the coordination of nickel with N, O of ligands.
3.2 PXRD
The PXRD diffraction pattern of hexagonal regularity pure MCM-41 has three reflection peaks viz., d100, d110 and d200, whereas Ni-MCM-41 and recovered catalyst have shown only one peak at d100 (Fig. 3). This observation indicates the tethering of nickel complex on the MCM-41[46].
3.3 SEM, EDX and ICP-OES
The SEM analysis was performed to study the surface morphology of the MCM-41 and Ni-MCM-41(Figs. 4a & c). These images show the uniformity in the surface morphology of both the compounds and there is no significant variation in the mesostructure of the Ni-MCM-41 catalyst even after the implantation of the mixed ligand metal complex on MCM-41.
The EDX spectrum of MCM-41 shows the existence of elements such as Si and O whereas the spectrum of Ni-MCM-41 shows the presence of Si, O along with Ni and N. It reveals the tethering of nickel complex on MCM-41. The weight and atomic percentage of elements present in the material are given as an inset picture in EDX spectra (Figs. 4b & d). It is clearly ratified the anchoring of the Ni-complex on the surface of the MCM-41 material. Based on the ICP-OES technique, Ni metal content in the catalyst was found to be 1.4 X 10− 3 mol/g on MCM-41.
3.4 Transmission electron microscopy
Figure 5 depicts the TEM image of Ni-MCM-41. It shows the particles have a regular hexagonal honeycomb-like structure, similar to the morphology of pure MCM-41. This approves the immobilization of Ni-complex on MCM-41 doesn’t affect the morphology of the catalyst.
3.5 N2 adsorption-desorption isotherm
The immobilization of mixed ligand metal complex on MCM-41 is further supported by the nitrogen adsorption-desorption isotherm. The mesoporosity of the MCM-41 and Ni-MCM-41 materials is confirmed by their type-IV isotherm [47]. The BET surface area, pore volume and pore size of Ni-MCM-41 have lower values when compared to that of the parent material, MCM-41 (Table 1 & Fig. 6) which suggests the tethering of metal complex on MCM-41.
Table 1
Surface properties of MCM-41and Ni-MCM-41
|
Entry |
Materials |
Surface area (m2 / g) |
Pore volume (cm3 / g) |
Pore size (Å) |
|---|---|---|---|---|
|
1. |
MCM-41 |
902.79 |
0.77 |
38.3 |
|
2. |
Ni-MCM-41 |
344.26 |
0.19 |
22.2 |
3.6 Thermogravimetric analysis
The thermal stability and the fraction of volatile components of the catalyst was analysed by thermogravimetric analysis. The TGA curve of the catalyst shows four-step weight losses (Fig. 7) between 45–157, 157–405, 405–721 and 721–936 oC. In the first step, weight loss at a lower temperature is ascribed to the removal of adsorbed water. The consecutive second and third weight losses are associated with the decomposition of the organic functional groups. At high temperature, the final weight loss is attributed to the decomposition of silanol groups.
3.7 Catalytic activity
The new mixed ligand Schiff base Ni-complex on MCM-41 was used as catalyst for the synthesis of 5-substituted-1H-tetrazoles via one pot three component reactions of various aldehydes, hydroxylamine and sodium azide. These reactions were carried out under two different energy supplying methods namely, thermal heating and microwave irradiation. The effectiveness of the two methods are compared in terms of the reaction time, yield, turn over number and turn over frequency.
Initially, the reaction of o-vanillin, hydroxylamine and sodium azide under the conventional method was selected as a model reaction for optimizing the reaction conditions. When the experiment was carried out in the absence of catalyst in DMF at 120 oC for 6 h, the preferred product was attained with only a poor yield of 47% (Table 2, entry 8). Hence, we tested different amounts of Ni-MCM-41 as a reusable catalyst at 20, 30, 40 and 50 mg in the model reaction. It was observed that the best catalyst loading is 40 mg for this reaction (entry 7) as the yield of the product remained constant while increasing the amount of catalyst used from 40 mg to 50 mg (entries 7, 9,10 & 11).
Table 2
Effect of solvents, temperature, catalyst amount and time for the synthesis of tetrazole derivatives reaction
|
Entry |
Solvent |
Temperature |
Catalyst (mg) |
Time (min / h) |
Yield (%) |
|---|---|---|---|---|---|
|
1. |
Ethanol a |
Reflux |
40 |
6 h |
52 |
|
2. |
Acetonitrile a |
Reflux |
40 |
6 h |
64 |
|
3. |
DMSO a |
100 oC |
40 |
6 h |
69 |
|
4. |
Toluene a |
110 oC |
40 |
6 h |
71 |
|
5. |
DMF a |
80 oC |
40 |
6 h |
69 |
|
6. |
DMF a |
100 oC |
40 |
6 h |
77 |
|
7. |
DMF a |
120 oC |
40 |
6 h |
90 |
|
8. |
DMF b |
120 oC |
- |
6 h |
47 |
|
9. |
DMF a |
120 oC |
20 |
6 h |
65 |
|
10. |
DMF a |
120 oC |
30 |
6 h |
74 |
|
11. |
DMF a |
120 oC |
50 |
6 h |
90 |
|
12. |
DMF c |
120 oC |
40 |
5 min |
54 |
|
13. |
DMF c |
120 oC |
40 |
10 min |
73 |
|
14. |
DMF c |
120 oC |
40 |
20 min |
80 |
|
15. |
DMF c |
120 oC |
40 |
30 min |
94 |
|
16. |
DMF c |
120 oC |
40 |
40 min |
94 |
Reaction conditions: (1 mmol) NH2OH.HCl, (1 mmol) NaN3, (1 mmol) o-vanillin, Ni-MCM-41 as catalyst (40 mg, 0.586 mol %) in DMF (5 ml) at 120 oC for conventional method- 6 h a/ microwave method − 30 min c
Reaction carried out under neat condition (without catalyst) b
In general, solvent plays a key role in chemical transformations in terms of reaction time and yield of the product. By considering the use of green solvent, we have also tried a reaction in polar protic solvent, ethanol, resulted in only poor yield (entry 1, 52%). Polar aprotic solvents such as acetonitrile and DMSO also gave only moderate yields (entries 2 & 3) while excellent yield was obtained in DMF (entry 7). The non-polar solvent, toluene, has also given only moderate yield (entry 4). Based on the above studies, DMF was found to be the better solvent over other solvents, similar to most of the reports on tetrazole synthesis. Among the different temperatures tested, it was found that the maximum yield was obtained at 120 oC.
Further, the effect of reaction time in the presence of the catalyst was also investigated. Upon tuning the reaction time, microwave irradiation method shows much superiority over conventional heating in terms of yield and time, 94% in 30 min instead of 90% in 6 h (entries 15 & 7).
Under optimized conditions, the reactions of aldehydes with hydroxylamine hydrochloride and sodium azide in DMF at 120 oC in the presence of Ni-MCM-41 as a catalyst gave 5-substituted 1H-tetrazoles in good to excellent yields (Table 3). It was observed that this optimized reaction condition is well suitable for the conversion of the following aldehydes to tetrazoles: i) substituted aromatic aldehydes with a wide range of electron-withdrawing (entries 2–4) / electron donating groups (entries 5 & 6), ii) multi-substituent groups (entries 7 & 8), iii) fused aromatic aldehyde (entry 9), iv) heteroaromatic aldehydes (entries 10–12) v) aromatic aldehyde with extended conjugation (entry 13) and vi) aliphatic aldehydes (entries 14 & 15).
Table:3
Synthesis of various tetrazoles by Ni-MCM-41 catalyst a
a Reaction conditions: (1 mmol) NH2OH.HCl, (1 mmol) NaN3, (1 mmol) aldehyde, Ni-MCM-41 as catalyst (40 mg, 0.586 mol %) in DMF (5 ml) at 120 oC for conventional method 6 h and microwave method 30 min
b Isolated yield
c Turnover number (TON) = (mmol of product)/ (mmol of catalyst) after time t
d Turnover frequency (TOF) = TON/time (h− 1)
Aromatic aldehyde bearing electron-withdrawing group at the para position (entry 3) results good yield over the substrate with m-substituent (entry 4). This may be due to the facile nature of the substrate with p-substituent. Aromatic aldehydes with electron donating groups such as -OH & -OCH3 (entries 5 & 6) exhibit good yields. Moreover, substrates with multi-substituents, p-vanillin and o-vanillin (entries 7 & 8) exhibit excellent yields. Here, it is noted that o-vanillin gave more yield than p-vanillin. This may be due to the hydroxyl group at 2-position (o-vanillin) increases the electrophilicity of carbonyl carbon of aldehyde by H- bonding whereas at 4-position (p-vanillin) it shows only electron-donating property [48]. Our catalyst has shown very good yields over the substrates of fused aromatics (entry 9) and heterocycles (entries 10–12). The extended conjugation aromatic aldehyde (entry 13) displays moderate yield (75%) whereas aliphatic aldehydes (entries 14 & 15) have offered lower yields (53–54%). These results show that the Ni-MCM-41 is a highly efficient catalyst for the conversion of different aldehydes to tetrazoles irrespective of the electronic properties of the substituents except aliphatic aldehydes.
To compare the catalytic activity of MCM-41, pure Ni-complex and Ni-MCM-41, an aldehyde to tetrazole conversion was performed in the model reaction under microwave irradiation using these catalysts (Fig. 8). The catalyst Ni-MCM-41 shows a preeminent high percentage yield than the other catalysts. It reveals the crucial role of mixed ligand Ni-complex embedded on highly ordered mesoporous structure of Ni-MCM-41 over mere MCM-41 and Ni-complex in the synthesis of tetrazoles.
By comparing the effectiveness of two different energy sources, microwave irradiation technique shows much superiority over conventional heating, not only in terms of lesser reaction time and higher yield but also in terms of much better TON and TOF of the catalytic reactions (Table 3).
The recoverability and reusability of the catalyst was tested in a model reaction under microwave irradiation (Fig. 9). The catalyst was removed by convenient filtration after each cycle and it was reused for five consecutive cycles without any considerable weight loss which indicates the good re-utility of the catalyst with effective catalytic performance. This may be due to the influence of mesoporosity of the material which is almost unaltered even after five cycles.
To illustrate the efficiency of the Ni-MCM-41 catalyst, the catalytic activity is compared with other reported catalysts and is given in Table 4. Though the catalysts on entries 1 and 5 were afforded better yields (96%) than our catalyst (entry 9, 94%) those reactions have been carried out under homogeneous condition and long reaction time (8 h / 12 h). The nano Fe3O4 catalyst (entry 8) gave 92% yield under microwave irradiation, solvent free condition, with the reaction time of 35 min. These results show that our system is comparable or better than other reports on the synthesis of tetrazoles. and it possesses i) economical catalyst ii) environmentally benign- microwave irradiation iii) shorter reaction time and iv) reusability nature.
Table 4
Comparison of efficiency of Ni-MCM-41 as a catalyst against the literature reports in synthesis of 5-substituted − 1H-tetrazole derivatives. a
|
Entry |
Catalyst |
Conditions |
Yield (%) |
Reference |
|---|---|---|---|---|
|
1. |
Ru (p-cymene) (Cl) (L3) |
DMF, 140 oC, 8h |
96 |
[49] |
|
2. |
(NH4)2 Ce (SO4)4.2H2O |
DMF, reflux, 5h |
72 |
[48] |
|
3. |
P2O5 |
DMF, reflux, 4h |
90 |
[50] |
|
4. |
I2 |
NH3, THF, RT, 8h |
90 |
[51] |
|
5. |
Cu(OAc)2 |
DMF, 120 oC, 12h |
96 |
[21] |
|
6. |
Nano Cu2O-MFR |
DMF, 100 oC, 8h |
92 |
[22] |
|
7. |
Cu-MCM-41 |
DMF, 140 oC, 12h |
90 |
[23] |
|
8. |
Nano Fe3O4 |
Solvent free, 80 oC, microwave irradiation, 35 min |
92 |
[52] |
|
9. |
Ni-MCM-41 |
DMF, 120 oC, microwave irradiation, 30 min |
94 |
This work |
a 5-substituted-1H-tetrazole derivative of benzaldehyde, NH2OH.HCl / NH3 / CH(CN)2 and azide.
The plausible mechanism for the synthesis of 5-substituted 1H-tetrazoles from aldehydes was represented in Scheme 3 using Ni-MCM-41 as a catalyst. Foremost, oxime is formed on the aldehyde under the activation of the carbonyl group of the aldehyde followed by a nucleophilic attack of the nitrogen atom of hydroxylamine. Subsequently, the nitrile product is formed by the elimination of water molecule. The Ni-MCM-41 catalyst activates the nitrile, which in turn initiates the immediate cyclization reaction between the nitrile and azide moiety and leads to the formation of tetrazole intermediate III. Then, the catalyst was removed through filtration, followed by acidification using HCl, the product IV was obtained.
3.8 Selected spectral data for 5-substituted-1H-tetrazole derivatives (supporting information)
S 1 : 2-methoxy-6-(1H-tetrazol-5-yl) phenol (Table 3, entry 8): H1 NMR (400 MHz, DMSO): δH = 3.88 (s, 3H, -OCH3), 6.96-7.00 (t, 1H, Ar-H), 7.16–7.18 (d, 1H, Ar-H), 7.52–7.54 (d, 1H, Ar-H), 10.41 (s, 1H, -NH), 15.14 (s, 1H, -OH) ppm.
S 2 : 1-(1H-tetrazol-5-yl)naphthalen-2-ol (Table 3, entry 9) : H1 NMR (400 MHz, DMSO): δH = 7.29–8.11 (m, 6H, Ar-H), 10.90 (s, 1H, -NH), 11.68 (s, 1H, -OH) ppm.
S 3 : 5-(1H-pyrrol-2-yl)-1H-tetrazole (Table 3, entry 10) : H1 NMR (400 MHz, DMSO): δH = 6.69–7.30 (m, 3H, Ar-H), 11.93 (s, 1H, -NH), 12.02 (s, 1H, -NH) ppm.
3.9 Hot filtration test
To appraisal whether the catalyst is functioning in a heterogeneous manner, we executed a hot filtration test for the model reaction which was subjected to microwave irradiation at 120°C for 30 min. At this time, the catalyst was detached from the reaction mixture and the experiment was pursued with filtrate for an additional 30 min. We found that the yield of the product was not increased (94% and 93.6% yield of before and after the test), which indicates that there is no metal leaching in this catalytic reaction.
In conclusion, we have designed an efficient green catalyst using Ni-Schiff base complex of mixed ligands on MCM-41 and used it for the synthesis of 5-substituted-1H-tetrazole derivatives by greener strategy. The exclusive features of this protocol contain (i) The use of commercially available and low-cost chemicals, (ii) One pot three component synthetic strategy (iii) Microwave irradiation (iv) Wide scope of substrates aryl, aryl of extended conjugation, heterocyclic and aliphatic (v) Less reaction time (vi) good yield and (vii) recoverability by simple filtration and reusability of heterogeneous catalyst.
Acknowledgements
The authors are grateful for the financial support from the University Grants Commission (UGC-BSR) F.30-319/2016 (BSR) Government of India, New Delhi, India. The first author acknowledges to University Grant Commission-Rajiv Gandhi National Fellowship (UGC-RGNF) (Grant No: RGNF-2015-17-SC-TAM-21024) research grant for their financial support.
Author Information
Affiliations
Department of Chemistry, Periyar University, Salem-636011, Tamil Nadu, India.
M. Bharathi, S. Indira, G. Vinoth, C. Denzil Britto, K. Shanmuga Bharathi.
Contributions
M. Bharathi: Conceptualization, Investigation, Methodology, Software, Writing- review & editing. S. Indira and G. Vinoth: Resources and Software. C. Denzil Britto: Software, Resources, Validation. K. Shanmuga Bharathi: Data curation, Resources, Supervision, Validation, Writing- review & editing.
Corresponding Author
Correspondence to: K. Shanmuga Bharathi.
Funding
This study was funded by University Grants Commission (UGC-BSR) F.30-319/2016 (BSR) / Rajiv Gandhi National Fellowship (UGC-RGNF) (Grant No: RGNF-2015-17-SC-TAM-21024), Government of India, New Delhi, India.
Data Availability:
The datasets used and/or analysed during the current study are available from the corresponding author on reasonable request.
Ethics Approval: The authors declare that all procedures followed were in accordance with the ethical standard.
Consent to Participate: All the authors have declare their consent to participate in this research article.
Consent for Publication: All the authors have declare their consent to publish this research article upon acceptance.
Research Involving Human Participants and/or Animals: Not applicable. Informed Consent: Not applicable.
Conflict of Interest: The authors also declare that there is no conflict of interest associated with this work.
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Scheme 1-3 are available in Supplementary Files section.
No competing interests reported.
- Supportingfile.docx
- Scheme1.png
Scheme: 1 Synthesis of Ni-MCM-41
- Scheme2.png
Scheme: 2 Synthesis of tetrazole derivatives
- Scheme3.png
Scheme:3 Plausible mechanism for the synthesis of tetrazole derivatives
