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Short Note

Ethyl 2-(2-((6-Methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate

by
Adriana Grozav
1,
Cristina Azarov
1,
Gabriel Marc
1,
Adrian Pîrnău
2,*,
Stanimir Manolov
3,
Ovidiu Oniga
4 and
Ovidiu Crișan
1
1
Department of Organic Chemistry, Faculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy, 8 Victor Babes, 400012 Cluj-Napoca, Romania
2
National Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donath Street, 400293 Cluj-Napoca, Romania
3
Department of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 24 “Tsar Assen” Street, 4000 Plovdiv, Bulgaria
4
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, 400012 Cluj-Napoca, Romania
*
Author to whom correspondence should be addressed.
Molbank 2026, 2026(1), M2127; https://doi.org/10.3390/M2127
Submission received: 4 December 2025 / Revised: 13 January 2026 / Accepted: 19 January 2026 / Published: 22 January 2026
(This article belongs to the Collection Heterocycle Reactions)
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Abstract

This study presents the synthesis of a new compound, ethyl 2-(2-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazinyl)thiazole-4-carboxylate, obtained by the Hantzsch heterocyclisation reaction. The compound was analyzed through melting point determination, 1H and 13C NMR spectroscopy, infrared, and UV spectroscopy.

Graphical Abstract

1. Introduction

Chromone (benzo-γ-pyrone) is a heterocyclic compound that occurs in a wide variety of natural or synthetic compounds with different biological activities, such as antibacterial [1,2], antifungal [3,4] antioxidant [5,6,7], antimalarial [8], and anti-Alzheimer [9] activities. Chromone derivatives have also shown promising anticancer activity [10,11] and may be useful in the treatment of COVID-19 [12]. Other remarkable properties of chromone-derived molecules include α-glucosidase inhibition [13], anti-inflammatory [14], antiallergic, and antiulcer activities [15]. This versatile molecule, capable of interacting with different types of receptors, can be considered a starting point for the synthesis of new medicinal compounds.
On the other hand, the thiazole moiety has attracted considerable attention due to its presence in compounds exhibiting antibacterial [16,17], antifungal [18,19,20,21], antimalarial [22], antiviral [23,24], α-glucosidase inhibition [25,26,27], anti-inflammatory [17,28,29], anticonvulsant [23], antiallergic [23], and antiulcer activity [17,29,30].
The hydrazine–thiazole moiety, in particular, has attracted considerable attention due to its presence in compounds exhibiting antioxidant [31,32] and antiproliferative activities [33]. Moreover, several other pharmacological properties, such as antifungal [18,34] and anti-inflammatory [35] effects, have also been reported in compounds with a hydrazone functional group.
Chromone–thiazole hybrid compounds with a hydrazone linker were previously reported in the literature and exhibited very good antioxidant activity, representing a good working hypothesis for obtention of the title compound from the present paper [36].

2. Results

Chemical Synthesis

The synthesis of new ethyl 2-(2-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate (3) was performed in two steps as presented in Scheme 1. First, the condensation of 6-methyl-4-oxo-4H-chromene-3-carbaldehyde (1) with hydrazinecarbothioamide (thiosemicarbazide) yielding 2-((6-methyl-4-oxo-4H-chromen-3-yl)methylene]thiosemicarbazone (2) [37,38], which was followed by its heterocyclisation with ethyl 3-bromo-2-oxopropanoate in a Hantzsch-type reaction in anhydrous DMF. Some attempts were made to synthesize compound 3 using acetone, ethanol, and acetic acid alone or as mixture of solvents at reflux, but due to the reduced solubility of intermediate 2, large volumes of solvent were required, and total conversion of intermediate 2 was not achieved; even some unwanted compounds were identified by TLC, and the respective synthesis were abandoned.

3. Discussion

In this study, we successfully synthesized a new hybrid molecule incorporating a chromone core and a thiazole moiety, interconnected through a hydrazone linker. The structural design was inspired by previous reports highlighting the strong antioxidant potential of chromone-based scaffolds [5,6,7], as well as the redox versatility characteristic of thiazole derivatives. Our working hypothesis was that combining these two heterocyclic systems into a single conjugated framework may enhance electron-donating properties and, consequently, free-radical neutralization capacity.

4. Materials and Methods

4.1. Chemical Synthesis

All reagents and chemicals were obtained from commercial sources (Sigma-Aldrich, subsidiary of Merck KGaA, Darmstadt, Germany) and used as received without further purification. The 1H-NMR and 13C-NMR spectra were recorded in DMSO-d6 using a Bruker Avance NMR spectrometer (Bruker, Karlsruhe, Germany). The IR spectra were recorded using a FT/IR 6100 spectrometer (Jasco, Cremella, Italy). The uncorrected melting point was measured with a Buchi M-560 device (BÜCHI Labortechnik AG, Flawil, Switzerland). The UV-vis spectrum was recorded with an UV-VIS Jasco V-530 spectrophotometer (Jasco International Co., Tokyo, Japan). Thin-layer chromatography (TLC) was performed on 0.2 mm silica gel 60 plates (Merck KGaA, Darmstadt, Germany).

4.1.1. Synthesis Protocol of 2-((6-Methyl-4-oxo-4H-chromen-3-yl)methylene]thiosemicarbazone (Intermediate Compound 2)

To a boiling solution of 6-methyl-4-oxo-4H-chromene-3-carbaldehyde 1 (1.88 g, 10 mmol) in 150 mL ethanol, hydrazinecarbothioamide was added (0.91 g, 10 mmol). A drop of concentrated acetic acid was added as catalyst. The solution was stirred under reflux for 3 h. The reaction progress was monitored by TLC (heptane/ethyl acetate/ethanol 7/3/0.5 v/v/v). After the reaction completed, the mixture was left to cool overnight to room temperature, and the resulting solid mass was filtered. The crude solid was dried using vacuum and crystallized from ethanol, obtaining a light yellow powder of thiosemicarbazone 2 (yield = 78%). The intermediate compound 2 was previously reported in the literature [36,37].

4.1.2. Synthesis Protocol of Ethyl 2-(2-((6-Methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate (Compound 3)

A mixture of 2-((6-methyl-4-oxo-4H-chromen-3-yl) methylene] thiosemicarbazone 2 (0.522 g, 2 mmol) and ethyl 3-bromo-2-oxopropanoate (0.41 g, 2.1 mmol) in 5 mL DMF was stirred at room temperature for 24 h. The reaction progress was monitored by TLC (heptane/ethyl acetate/ethanol 7/3/0.5 v/v/v); after the reaction completed, the mixture was neutralized to pH = 7 with NaHCO3 aqueous solution (10%). The resulting precipitate was filtered, dried using vacuum, and recrystallized from DMF, obtaining a pale yellow powder.
Ethyl 2-(2-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate (compound 3): Pale yellow solid (m. p. 248 °C), yield 63% (0.45 g), 1H-NMR (DMSO-d6, 500 MHz) δ (ppm): 1.282 (t, 3H, J = 7.00 Hz), 2.444 (s, 3H), 4.241 (q, 2H, J = 7.00 Hz), 7.613 (d, 1H, J = 8.5 Hz), 7.667 (dd, 1H, J1 = 8.5 Hz and J2 = 2.5 Hz), 7.774 (s, 1H), 7.910 (s, 1H), 8.105 (s, 1H), 8.707 (s, 1H), 12.326 (s, 1H). 13C-NMR: (DMSO-d6, 125 MHz) δ (ppm): 14.1, 20.4, 60.3, 118.1, 118.4, 119.1, 122.9, 124.4, 134.2, 135.6, 142.7, 153.6, 154.1, 160.9, 167.7, 169.6, 174.6; IR νmax (cm−1): 3208 (νNH), 3119, 2982 (νC–H), 1717, 1620 (νC = O), 1568–1585 (νC = N), 1214 (νC–O); UV-VIS: (40 mM in DMSO): 280 nm, 380 nm.

Supplementary Materials

The following supporting information is available online. Figure S1: The IR spectrum of compound 3. Figure S2: The 1H NMR spectrum of the compound 3. Figure S3: The 13C NMR spectrum of compound 3. Figure S4: The UV-VIS spectrum of compound 3 (40 mM in DMSO).

Author Contributions

Conceptualization, G.M., S.M., O.O. and O.C.; methodology, A.G., C.A., O.O. and G.M.; software, G.M.; validation, O.C., S.M., O.O. and O.C.; formal analysis, G.M. and C.A.; investigation, C.A., G.M. and A.P.; resources, A.G., O.O. and G.M.; data curation, A.G., G.M. and O.C.; writing—original draft preparation, A.G., G.M., O.O. and S.M.; writing—review and editing, A.G., C.A., G.M., S.M. and O.C.; supervision, O.O. and O.C.; project administration, O.O. and O.C.; funding acquisition, O.O. and A.P. All authors have read and agreed to the published version of the manuscript.

Funding

This work was supported through the “Nucleu” Program within the National Research Development and Innovation Plan 2022–2027, Romania, carried out with the support of MEC, project no. 27N/03.01.2023, component project code PN 23 24 01 05 and through the Installations and Special Objectives of National Interest (IOSIN), IZOSTAB.

Data Availability Statement

The original contributions presented in this study are included in the article/Supplementary Material. Further inquiries can be directed to the corresponding author.

Conflicts of Interest

The authors declare no conflicts of interest.

Abbreviations

The following abbreviations are used in this manuscript:
DMFDimethylformamide
DMSODimethyl sulfoxide
M.P.Melting Point

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Molbank 2026 m2127 sch001
Scheme 1. Synthesis route followed for obtention of ethyl 2-(2-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate (3).
Scheme 1. Synthesis route followed for obtention of ethyl 2-(2-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate (3).
Molbank 2026 m2127 sch001
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MDPI and ACS Style

Grozav, A.; Azarov, C.; Marc, G.; Pîrnău, A.; Manolov, S.; Oniga, O.; Crișan, O. Ethyl 2-(2-((6-Methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate. Molbank 2026, 2026, M2127. https://doi.org/10.3390/M2127

AMA Style

Grozav A, Azarov C, Marc G, Pîrnău A, Manolov S, Oniga O, Crișan O. Ethyl 2-(2-((6-Methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate. Molbank. 2026; 2026(1):M2127. https://doi.org/10.3390/M2127

Chicago/Turabian Style

Grozav, Adriana, Cristina Azarov, Gabriel Marc, Adrian Pîrnău, Stanimir Manolov, Ovidiu Oniga, and Ovidiu Crișan. 2026. "Ethyl 2-(2-((6-Methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate" Molbank 2026, no. 1: M2127. https://doi.org/10.3390/M2127

APA Style

Grozav, A., Azarov, C., Marc, G., Pîrnău, A., Manolov, S., Oniga, O., & Crișan, O. (2026). Ethyl 2-(2-((6-Methyl-4-oxo-4H-chromen-3-yl)methylene)hydrazineyl)thiazole-4-carboxylate. Molbank, 2026(1), M2127. https://doi.org/10.3390/M2127

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