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12 November 2025

Synthesis and Spectral Characteristics of N-(1-(((2E,4E)-6-(2-Bromophenyl)-3-cyclohexyl-2-(cyclohexylimino)-2,3-dihydro-4H-1,3,5-oxadiazin-4-ylidene)amino)-2,2,2-trichloroethyl)acetamide †

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Department of Pharmacy, Chemistry and Technologies, Ukrainian State University of Science and Technologies, Lazariana St., 2, 49010 Dnipro, Ukraine
*
Author to whom correspondence should be addressed.
†
Presented at the 29th International Electronic Conference on Synthetic Organic Chemistry, 14–28 November 2025; Available online: https://sciforum.net/event/ecsoc-29.
Chem. Proc.2025, 18(1), 77;https://doi.org/10.3390/ecsoc-29-26847
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Abstract

This work presents a step-by-step synthesis of a new derivative of 1,3,5-oxadiazine. In the first step, by reacting N-(1-amino-2,2,2-trichloroethyl)acetamide with 2-bromobenzoyl isothiocyanate, a previously undescribed thiourea, N-((1-acetamido-2,2,2-trichloroethyl)carbamothioyl)-2-bromobenzamide, was obtained. In the next step, this compound was treated with dicyclohexylcarbodiimide (DCC), resulting in cyclization and the formation of a new derivative of 1,3,5-oxadiazine-N-(1-(((2E,4E)-6-(2-bromophenyl)-3-cyclohexyl-2-(cyclohexylimino)-2,3-dihydro-4H-1,3,5-oxadiazin-4-ylidene)amino)-2,2,2-trichloroethyl)acetamide. The reaction was carried out in acetonitrile at reflux for one hour. Presumably, in the first step of the transformation, under the action of DCC, the elimination of a hydrogen sulfide molecule occurs with the formation of an intermediate carbodiimide derivative-N-(((1-acetamido-2,2,2-trichloroethyl)imino)methylene)-2-bromobenzamide. This intermediate then undergoes a [4+2] cycloaddition reaction with another DCC molecule to form the desired 1,3,5-oxadiazine product in 82% yield. Its structure was confirmed by NMR spectroscopy (1H and 13C).

1. Introduction

In recent decades, 1,3,5-oxadiazine derivatives have attracted growing attention across various scientific fields [1,2,3,4,5,6]. Compounds containing the 1,3,5-oxadiazine ring are considered in pharmacy and medicine as potential chemotherapeutic agents [4], as well as antibacterial [7,8,9,10,11,12] and antifungal agents [10,11]. They are also important in agriculture as insecticides (e.g., thiamethoxam [13,14] and its analogues [15,16]), herbicides [17], and larvicides [18,19,20]. Beyond biological activity, these compounds serve as valuable synthons and catalysts in organic synthesis and have been applied in the production of ionic liquids [21], polymers [22], and explosives [23]. Cucurbit[n]uryls incorporating a 1,3,5-oxadiazine ring are of particular interest in supramolecular chemistry for constructing molecular clips [24,25,26,27,28,29,30,31,32,33].
Most 1,3,5-oxadiazines are synthetic; only two natural representatives are known [34,35]. Their main synthetic routes involve [4+2]-cycloaddition [8,9,10,11,17,18,19,36,37,38,39,40], intramolecular cyclization of diols [15,16,23,41,42,43,44,45,46], bisamidials [47], or substituted thioureas [48,49,50]. Recently, their preparation via transformation of other heterocyclic systems has also been reported [23,51]. This article describes the synthesis of a new 1,3,5-oxadiazine derivative: N-(1-(((2E,4E)-6-(2-bromophenyl)-3-cyclohexyl-2-(cyclohexylimino)-2,3-dihydro-4H-1,3,5-oxadiazin-4-ylidene)amino)-2,2,2-trichloroethyl)acetamide.

2. Materials and Methods

Spectral studies, including 1H NMR (400 MHz) and 13C NMR (100 MHz), were conducted on DMSO-d6 solutions using a Varian Agilent VNMRS 400 MHz spectrometer (Agilent Technologies, Inc., Santa Clara, CA, USA). Residual solvent signals served as internal standards. Elemental analysis was performed with a LECO CHNS-900 instrument (LECO Corporation, St. Joseph, MI, USA). The reaction progress and purity of the synthesized compounds were monitored by thin-layer chromatography on Silufol UV-254 plates (Serva-Feinbiochemica GmbH & Co, Heidelberg, Germany) with a chloroform and acetone (3:1) eluent ratio. Melting points were determined in open capillaries.
Synthesis of N-((1-acetamido-2,2,2-trichloroethyl)carbamothioyl)-2-bromobenzamide (3). A solution of 10 mmol of 2-bromobenzoyl isothiocyanate (2) in 10 mL of acetonitrile was added to 10 mmol (2.05 g) of N-(1-amino-2,2,2-trichloroethyl)acetamide (1) [52] in 15 mL of MeCN. The mixture was brought to a boil and left at room temperature for 12 h. The resulting precipitate of thiourea (3) was filtered, washed with 10 mL of acetonitrile, and purified by recrystallization from methanol. Pale yellow crystals; yield 89% (3.98 g); mp 190–192 °C (MeOH); Rf = 0.74. 1H NMR: δ 12.25 (s, 1H, NH), 11.54 (d, J = 9.3 Hz, 1H, NH), 9.25 (br. s, 1H, NH), 7.71 (d, J = 7.3 Hz, 1H, Harom.), 7.57 (d, J = 7.3 Hz, 1H, Harom.), 7.51–7.44 (m, 2H, Harom.), 7.27 (dd, J = 8.8, 9.3 Hz, 1H, CH), 1.97 (s, 1H, NH). Anal. Calcd (%) for C12H11BrCl3N3O2S (447.55): C, 32.20; H, 23.76; N, 9.39; S, 7.16. Found: C, 32.13; H, 23.71; N, 9.45; S, 7.22.
Synthesis of N-(1-(((2E,4E)-6-(2-bromophenyl)-3-cyclohexyl-2-(cyclohexylimino)-2,3-dihydro-4H-1,3,5-oxadiazin-4-ylidene)amino)-2,2,2-trichloroethyl)acetamide (5). A mixture of 10 mmol of thiourea 3 and 20 mmol (4.13 g) of dicyclohexylcarbodiimide was added to 40 mL of dry acetonitrile and refluxed for 40–50 min. The reaction mixture was cooled, and the precipitated crystals were filtered and washed with 10 mL of MeCN. The final product was purified by recrystallization from methanol. White crystals; yield 82% (5.08 g); mp 169–171 °C (MeOH); Rf = 0.75. 1H NMR: δ 8.50 (br. s, 1H, NH), 7.91 (d, J = 7.0 Hz, 1H, Harom.), 7.84 (d, J = 7.0 Hz, 1H, Harom.), 7.66–7.58 (m, 2H, Harom.), 6.78 (d, J = 8.8 Hz, 1H, CH), 4.81–4.75 (m, 1H, cyclohexyl), 3.79 (br. s, 1H, cyclohexyl), 2.75–2.59 (m, 2H, cyclohexyl), 1.91 (s, 3H, CH3), 1.82–1.12 (m, 18H, cyclohexyl). 13C NMR: δ 168.7 (C=O), 157.4 (C=N), 147.5 (C=N), 135.1 (C=N), 134.3, 134.0, 132.4, 129.9, 128.0, 120.7 (Carom.), 103.8 (CCl3), 72.4 (CH), 56.0, 52.5, 33.8, 33.6, 26.9, 26.1, 26.0, 25.5, 25.2, 23.7, 22.7 (cyclohexyl). Anal. Calcd (%) for C25H31BrCl3N5O2 (619.81): C, 48.45; H, 5.04; N, 11.30. Found: C, 48.39; H, 4.98; N, 11.38.

3. Results and Discussion

The starting compound, N-(1-amino-2,2,2-trichloroethyl)acetamide (1), was synthesized according to a previously reported procedure [52]. It readily reacted with 2-bromobenzoyl isothiocyanate (2), yielding N-((1-acetamido-2,2,2-trichloroethyl)carbamothioyl)-2-bromobenzamide (3) (Scheme 1). The product was obtained in almost quantitative yield, reaching approximately 89% after recrystallization. Subsequently, thiourea 3 was treated with dicyclohexylcarbodiimide (DCC). Under the influence of DCC, hydrogen sulfide was eliminated from thiourea 3, most likely leading to the formation of carbodiimide intermediate 4. This intermediate then participated in a [4+2] cycloaddition with an additional DCC molecule, affording the target oxadiazine 5.
Scheme 1. Synthesis of N-((1-acetamido-2,2,2-trichloroethyl)carbamothioyl)-2-bromobenzamide (3) and its cyclisation into 1,3,5-oxadiazine (5). Reagents and conditions: (a) MeCN, reflux 1–2 min, r.t. 12 h; (b) 2 DCC, MeCN, reflux 40–50 min, r.t. 1–2 h.
The structures of the synthesized compounds were confirmed by spectral analysis. In the 1H NMR spectrum of compound 3, signals corresponding to three NH protons were detected, along with a characteristic doublet–doublet signal from the CH proton of the alkylamide fragment. In contrast, the spectrum of oxadiazine 5 displayed a single NH proton signal and a doublet from the CH group. Additionally, the 1H NMR spectrum of compound 5 contained signals corresponding to 22 protons of two cyclohexyl rings, which is consistent with the [4+2] cycloaddition process. The 13C NMR data further corroborated the formation of oxadiazine 5, revealing the absence of the C=S signal, the presence of a single C=O signal at 168.7 ppm, and three C=N signals in the 157.4–135.1 ppm range.

4. Conclusions

In summary, we have developed a convenient and efficient method for the synthesis of a new 1,3,5-oxadiazine derivative. Our synthetic approach is based on the reaction of N-(1-amino-2,2,2-trichloroethyl)acetamide with 2-bromobenzoyl isothiocyanate, followed by DCC-mediated cyclization through a [4+2] cycloaddition mechanism. The target compound was obtained in high yield, demonstrating the effectiveness of the developed method. The structures of the intermediates and final product were confirmed by 1H and 13C NMR spectroscopy, which clearly indicated the transformation of thiourea into the oxadiazine core. The absence of the C=S signal and the presence of characteristic C=N signals supported the successful ring formation. This synthetic strategy provides a practical pathway for the preparation of structurally diverse oxadiazines. The results of our work may serve as a foundation for the further design of heterocyclic systems with potential biological activity.

Author Contributions

V.V.P.; methodology, formal analysis, investigation. P.V.Z.; conceptualization, methodology, writing—original draft, formal analysis, investigation, visualization, project administration. D.S.K.; methodology, formal analysis, investigation. O.V.O.; validation, resources, writing—review, and editing. V.V.K.; validation, resources, writing—review, and editing. A.V.K.; validation, supervision, writing—review, and editing. All authors have read and agreed to the published version of the manuscript.

Funding

The work has been carried out within the framework of the project “New principles of synthesis of fluorescent materials and biologically active N,S-containing heterocycles” (state registration number 0123U101168) funded by the Ministry of Education and Science of Ukraine.

Institutional Review Board Statement

Not applicable.

Data Availability Statement

Reported data are available from the authors via e-mail contact.

Conflicts of Interest

The authors declare no conflicts of interest.

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