Synthesis and spectral characterization of novel 1,3,5 triazines derivative with substituted amines

Introduction

The chemistry of heterocyclic compounds has always been a central area of research owing to their diverse structural features and broad spectrum of biological and industrial applications. Among these, 1,3,5-triazines represent an important class of nitrogencontaining heterocycles characterized by a symmetrical six-membered ring with alternating carbon and nitrogen atoms. Their unique electronic configuration imparts exceptional chemical stability and versatile reactivity, making them valuable scaffolds in pharmaceutical, agrochemical, polymer, and material sciences [1][2][3][4][5] . Triazine derivatives have been widely employed as anticancer, antimicrobial, antifungal, antiviral, and anti-inflammatory agents, while industrially they are key intermediates in resins, dyes, herbicides, UV stabilizers, and functional polymers. The presence of multiple substitution sites in the triazine ring provides opportunities for structural diversification through nucleophilic substitution reactions, enabling the systematic introduction of electrondonating, electron-withdrawing, or sterically demanding substituents. This versatility allows researchers to modulate physicochemical, thermal, and biological properties in a predictable manner [5][6][7][8][9][10] . In recent years, amine-substituted 1,3,5-triazines have attracted considerable attention due to their ability to form stable conjugates, hydrogen-bonding interactions, and biologically active frameworks. The incorporation of substituted amines often enhances lipophilicity, bioavailability, and receptor binding, thereby improving biological efficacy [11] . Moreover, the straightforward synthetic accessibility of these derivatives from cyanuric chloride (a readily available precursor) under mild conditions makes them excellent candidates for both structural exploration and activity optimization [12] . Comprehensive spectral characterization plays a crucial role in confirming the structures and substitution patterns of these compounds. Techniques such as FT-IR, UV-Vis, ¹H NMR, ¹³C NMR, mass spectrometry, and elemental analysis provide detailed insights into functional groups, electronic transitions, molecular frameworks, and overall composition. Furthermore, thermogravimetric analysis (TGA) is employed to assess the thermal stability and potential material applications of triazine derivative s [13][14][15][16][17][18][19][20] .

The present work focuses on the synthesis and detailed spectral characterization of novel 1,3,5-triazine derivatives substituted with various amines. By correlating structural modifications with spectral characterization, this study aims to expand the chemical diversity of triazines and identify new leads. And Techniques such as FT-IR, ¹H NMR, ¹³C NMR, mass spectrometry was tested for newly synthesised compounds.

Material and Methods

All the chemicals used were of analytical grade (AR) and used as received. Distilled water was used for the preparation of the solutions during analysis. The methodology constitutes the backbone of any scientific investigation, as it provides a systematic framework for conducting research and ensures the reliability, reproducibility, and validity of the results obtained. In the present study, the methodology was carefully designed to accomplish the primary objective of synthesizing, characterizing, and evaluating a large library of 1,3,5triazine derivatives. The approach combined both traditional organic synthesis techniques and modern analytical tools in order to obtain novel compounds with potential biological significance.

• General procedure for synthesis of 1,3,5 triazine derivatives with substituted acetophenone and cyclohexane methyl amines for Scheme-I

Step 1-Synthesis of 2-aminothiazole from substituted acetophenone In this step reaction of 1 molar thiourea and 1 molar substituted acetophenone in presence of Iodine and DMF was reflux about 3 hours to give 2-aminothiodiazole via a Hantzsch thiazole synthesis-like pathway. The iodine acts as an oxidant and cyclizing agent to facilitate the condensation and ring formation.

The progress of the reaction was monitored by TLC. After completion of reaction, the precipitate formed was filtered and washed with distilled water, dried and the crude product was recrystallized from ethanol to obtained product (3) (5.39 g, yield 94%) as Light-yellow crystals; Melting point, 86 to 89 °C; Solubility in water

Where, R = NH2, OH, Cl, OCH3, CH3, H, Br, CH2CH3.

Scheme 1: Synthesis of 2-aminothiazole from substituted acetophenone

Step 2: Reaction of substituted 2-aminothiazole with Cyanuric chloride

In this step reaction 4(a-h) was synthesised by the reaction of Cyanuric chloride (0.02 mol) with substituted 2aminothiodiazole (0.02 mol) in 25 cm 3 acetone methylene chloride and K 2 CO 3 at R.T with constant stirring for Four hours. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction was neutralised by crushed ice poured into the reaction mixture The precipitate formed was filtered and washed with distilled water, dried and the crude product was recrystallized from ethanol to obtained product (6.39 g, yield 95%) as pale-yellow powder M.P. 220°C.

Step 3: Synthesis of 1,3,5-triazine derivative from cyclohexane methyl amines

In this step (5a-h) was synthesised by using cyclohexane methyl amine (0.005 mol) and 4 (a-k) 0.005 mol) in methylene chloride 25 cm 3 . The reaction mixture was exposed under microwave irradiation at 140 watts for Ten min. The progress of the reaction was monitored by TLC.

After completion of reaction, the reaction was neutralised by 10% potassium carbonate solution and crushed ice poured into the reaction mixture The precipitate formed was filtered and washed with distilled water, dried and the crude product was recrystallized from ethanol to obtain 5 (a-h) (3.55 g, yield 92 %) as yellow powder M.P. 185°C. and same reaction will be carried out for different substituted benzophenone.

Where, R = NH2, OH, Cl, OCH3, CH3, H, Br, CH2CH3.

Scheme 3: Synthesis of 1,3,5-triazine derivatives from cyclohexane methyl amine.

General procedure for synthesis of 1, 3, 5-triazine derivatives for Scheme-II:

Results and Discussion Thin Layer Chromatography

The purity of compound was checked by the TLC by using solvent system ethyl acetate and Hexane ether ratio (1:4).

All the synthesized compounds were characterized by recording the Rf values in TLC. The Rf values from the TLC, of all the synthesized compounds are mentioned in Table No: 4 below [24][25][26] .

Spectral Characterization:

The spectral characterization of newly synthesized derivatives carried out by using FTIR, and 1 H NMR, 13 C NMR and Mass spectrometry.

Fourier Transform Infrared Spectroscopy (FTIR):

Infrared spectra of compound 1 to 16 provide valuable information regarding the nature of the functional groups present in ligand and its metal complexes. IR spectral technique has proved to be the most suitable one to arrive information related to nature of bonding of the ligand to the metal ion. The FTIR spectra for newly synthesised compounds are shown in Table No: 3 Thus, FTIR characterization provided clear evidence for the formation of the triazine nucleus and its derivatives, serving as a reliable tool to establish structural confirmation at the preliminary stage.

H NMR Spectral Study

Proton NMR Spectroscopy gives information about the type of protons; to study the number of equivalent protons and their environment thereby we can ascertain the structure of the molecule. The show characteristic peak pattern at 2.73 due to CH 2 1.18 due to CH 3 .and these values are good accord with literature survey [29][30][31][32][33][34][35] . The compound 6a show characteristic peak pattern at 5.42 due to NH 2 and patten of peak is singlet. Compound 6b show characteristic peak pattern at 9.67 due OH patten of peak is singlet, Compound 6d show characteristic peak pattern at 3.81 due to OCH 3 patten of peak is singlet Compound 6e show characteristic peak pattern at 2.34 due CH 3 and patten of peak is singlet Compound 6f show characteristic peak pattern at 7.86,7.39, 7.49 due to benzene ring and obtained patten of peak is dublet. Compound 6g show characteristic peak pattern at 7.76,7.55, and Compound 6h show characteristic peak pattern at 2.72 due to CH2 1.18 due to CH 3 . patten of peak is triplet and quartet and these values are good accord with literature survey [3640] .

The ¹H NMR spectra of the synthesized 1,3,5-triazine derivatives displayed well-resolved proton signals consistent with the proposed molecular structures. The absence of ring protons in the triazine core was evident, while the characteristic chemical shifts corresponding to the substituted amines, aromatic, aliphatic, or heteroatom-linked protons confirmed successful substitution on the triazine nucleus. The splitting patterns and integration values matched the expected number of protons in each environment, thereby validating the structural framework.

Overall, the ¹H NMR spectral analysis strongly supports the successful synthesis and structural confirmation of the 1,3,5triazine derivatives.

13 C NMR Spectral Studies ¹³C Nuclear Magnetic Resonance (NMR) spectroscopy is a powerful analytical technique used to elucidate the carbon skeleton of organic molecules and to confirm the presence of specific structural moieties. In the case of 1,3,5-triazine derivatives, ¹³C NMR provides critical information about the chemical environment of carbon atoms within the heteroaromatic ring as well as the attached substituents. The triazine ring typically shows characteristic downfield signals for the C=N carbons, which can be clearly distinguished from the resonances of the substituted aromatic or aliphatic carbons. The presence, position, and chemical shift of these signals serve as reliable markers for verifying successful substitution on the triazine nucleus. Thus, ¹³C NMR characterization not only complements FTIR, ¹H NMR, and mass spectral data but also offers definitive structural confirmation of the synthesized 1,3,5triazine derivatives.

It is similar to 1 H NMR or proton NMR, the identification of carbon atoms in an organic molecule just as proton NMR identifies hydrogen atoms. 13 C NMR detects only the 13 C isotope. The main carbon isotope, 12 C is not detected although much less sensitive than 1 H NMR spectroscopy. The 13 C NMR spectra of all newly synthesized 1,3,5-triazine derivatives are shown below in The newly synthesized s-triazines derivatives with substituted amines analyzed for 13 C NMR spectral characterization. It is similar to proton NMR ( 1 H NMR). The identification of carbon atoms in an organic molecule just as proton NMR identifies hydrogen atoms. 13 13 C NMR are good agreement with literature review [41 13 C NMR spectrum of Compound-6a in DMSO showed that NH 2 attached carbons in the benzene ring gives characteristic peak at 123.0, 128.3, 115.1 145.6 ppm, and peaks obtained at, 164.1, 159.3, 160.6 due to triazines. peaks obtained at 145.0,72.7 and 79.0 due to carbon in imines. alco peak obtained due carboxyl carbon at 177.5 and peak obtained at 160.6 and 105.0 due to carbon in thiazole. 13 C NMR spectrum of Compound-6b in DMSO showed that OH attached carbons in the benzene ring gives characteristic peak at 126.2, 128.9, 116.4, 158.5 ppm, and peaks obtained at, 164.1, 159.3, 160.6 due to triazines. peaks obtained at 145.0,72.7 and 79.0 due to carbon in imines. alco peak obtained due carboxyl carbon at 177.5 and peak obtained at 160.6 and 105.0 due to carbon in thiazole. 13 C NMR spectrum of Compound-6c in DMSO showed that Cl attached carbons in the benzene ring gives characteristic peak at 120.2, 128.7, 135.5 ppm, and peaks obtained at, 164.1, 159.3, 160.6 due to triazines. peaks obtained at 145.0,72.7 and 79.0 due to carbon in imines. alco peak obtained due carboxyl carbon at 177.5 and peak obtained at 160.6 and 105.0 due to carbon in thiazole. 13 C NMR spectrum of Compound-6d in DMSO showed that OCH 3 attached carbons in the benzene ring gives characteristic peak at 121.1, 159.8, 55.8 ppm, and peaks obtained at, 164.1, 159.3, 160.6 due to carbon in triazines. peaks obtained at 145.0,72.7 and 79.0 due to carbon in imines. alco peak obtained due carboxyl carbon at 177.5 and peak obtained at 160.6 and 105.0 due to carbon in thiazole. 13 C NMR spectrum of Compound-6e in DMSO showed that CH 3 attached carbons in the benzene ring gives characteristic peak at 131.2, 129.0, 128.9, 21.3 ppm, and peaks obtained at, 164.1, 159.3, 160.6 due to carbon in triazines. peaks obtained at 145.0,72.7 and 79.0 due to carbon in imines. alco peak obtained due carboxyl carbon at 177.5 and peak obtained at 160.6 and 105.0 due to carbon in thiazole. 13 C NMR spectrum of Compound-6f in DMSO showed that carbons in the benzene ring gives characteristic peak at 134.2, 128.3, 128.6, 127.9 ppm, and peaks obtained at, 164.1, 159.3, 160.6 due to carbon in triazines. peaks obtained at 145.0,72.7 and 79.0 due to carbon in imines. alco peak obtained due carboxyl carbon at 177.5 and peak obtained at 160.6 and 105.0 due to carbon in thiazole. 13 C NMR spectrum of Compound-6g in DMSO showed that Br attached carbons in the benzene ring gives characteristic peak at 133.2, 128.6, 131.5, 122.3 ppm, and peaks obtained at, 164.1, 159.3, 160.6 due to carbon in triazines. peaks obtained at 145.0,72.7 and 79.0 due to carbon in imines. alco peak obtained due carboxyl carbon at 177.5 and peak obtained at 160.6 and 105.0 due to carbon in thiazole. 13 C NMR spectrum of Compound-6g in DMSO showed that ethyl attached carbons in the benzene ring gives characteristic peak at 129.0, 127.6, 143.5, 28.2, 12.5 ppm, and peaks obtained at, 164.1, 159.3, 160.6 due to carbon in triazines. peaks obtained at 145.0,72.7 and 79.0 due to carbon in imines. alco peak obtained due carboxyl carbon at 177.5 and peak obtained at 160.6 and 105.0 due to carbon in thiazole. the above data obtained from 13 C NMR are good agreement with literature review [24][25][26][27][28] . The ¹³C NMR spectra of the synthesized 1,3,5-triazine derivatives provided conclusive evidence for the presence of the triazine nucleus and its substituents. The characteristic downfield signals observed for the C=N carbons of the triazine ring were consistent with the heteroaromatic environment, while the distinct chemical shifts for aromatic, aliphatic, and heteroatom-linked carbons confirmed the successful incorporation of the desired substituents. The number, intensity, and positions of the carbon signals matched well with the expected structural framework, and no extra peaks were observed, indicating good purity of the compounds. Thus, ¹³C NMR characterization strongly supports the successful synthesis and accurate structural confirmation of the 1,3,5-triazine derivatives.

Mass Spectrometry

The fragmentation patterns of all newly synthesized compound were reported in m/z values [29] . The Molecular Formulas and mass spectra details of all newly synthesized 1,3,5-triazine derivatives are shown below in Table No Newly synthesized 135 triazines derivatives namely 5a to 5h gives molecular ions peak at 492,494, 511, 508, 492, 478, 557, 506 and for 6a to 6h gives molecular ions peak at 548, 549, 568, 564, 547, 533, 612 561 respectively and these values are good agreement with literature review [42] . The mass spectra of the synthesized 1,3,5-triazine derivatives provided definitive confirmation of their molecular weights and molecular formulas. The observed molecular ion peaks corresponded closely with the calculated molecular masses, validating the successful formation of the targeted compounds. Fragmentation patterns further supported the proposed structures by displaying characteristic cleavage of substituents and the triazine ring, consistent with known fragmentation behaviour of similar heterocyclic compounds. The absence of significant unexpected peaks indicated high purity of the synthesized derivatives. Overall, mass spectral analysis corroborates the successful synthesis and structural integrity of the 1,3,5-triazine derivatives, complementing FTIR and NMR data in confirming their identity.

The synthesized 1,3,5-triazine derivatives were successfully characterized using FTIR, ¹H NMR, ¹³C NMR, and mass spectrometry, providing conclusive evidence of their structures and purity. FTIR analysis confirmed the presence of the triazine ring through characteristic C=N stretching vibrations and identified functional groups introduced via substitution. ¹H NMR spectra displayed well-resolved proton signals with chemical shifts, splitting patterns, and integration consistent with the proposed substituents, while the absence of ring protons confirmed the triazine core. ¹³C NMR spectra further supported the structure by showing downfield signals for the C=N carbons of the triazine nucleus along with resonances for aromatic, aliphatic, and heteroatom-linked carbons, consistent with the expected framework. Mass spectral data corroborated the molecular weights of the derivatives, with molecular ion peaks and fragmentation patterns aligning with the calculated structures and indicating high purity.

Collectively, these spectral techniques confirm the successful synthesis, structural integrity, and purity of the 1,3,5-triazine derivatives, providing a robust foundation for subsequent physicochemical and biological studies.

Conclusion

The spectral characterization of the synthesized 1,3,5triazine derivatives confirms the successful incorporation of the desired substituents and validates the proposed structures. FT-IR spectra clearly indicated the presence of characteristic absorption bands corresponding to the triazine ring vibrations, C=N stretching, and functional groups of the substituted amines. ¹H-NMR and ¹³C-NMR spectra provided detailed insights into the chemical environment of hydrogen and carbon atoms, showing well-defined signals consistent with the expected structural framework of the triazine nucleus and its substituents. The mass spectral data further corroborated the molecular weight of each compound, matching the calculated values, thereby confirming their purity and molecular integrity. Overall, the combined spectral analyses FT-IR, NMR, mass spectrometry unequivocally establish the formation of the targeted 1,3,5-triazine derivatives and provide a reliable basis for further exploration of their physicochemical and biological properties.

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