Molbank

9 pages, 1563 KB

Open AccessShort Note

5-(2-Methylsulfanylethyl)-3-prop-2-enyl-2-sulfanylideneimidazolidin-4-one

by Petar Stanić, Marko V. Rodić and Biljana Šmit

Molbank 2025, 2025(3), M2057; https://doi.org/10.3390/M2057 - 4 Sep 2025

An amino acid-derived 2-thiohydantoin, 5-(2-methylsulfanylethyl)-3-prop-2-enyl-2-sulfanylideneimidazolidin-4-one, obtained from l-methionine, was synthesized in a two-step reaction protocol with allyl isothiocyanate. The compound was obtained in an 82% yield and was fully structurally characterized by NMR and IR spectroscopy. The crystal structure, molecular packing, and [...] Read more.

An amino acid-derived 2-thiohydantoin, 5-(2-methylsulfanylethyl)-3-prop-2-enyl-2-sulfanylideneimidazolidin-4-one, obtained from l-methionine, was synthesized in a two-step reaction protocol with allyl isothiocyanate. The compound was obtained in an 82% yield and was fully structurally characterized by NMR and IR spectroscopy. The crystal structure, molecular packing, and intermolecular interactions were characterized by X-ray diffraction analysis. Full article

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5 pages, 585 KB

Open AccessShort Note

3-([4-(Acetylamino)phenyl]methoxy-1-carbonyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic Acid

by Kathryn N. Mayeaux, Bailey N. Baxter, Hannah K. Lawley, Caleb N. Lopansri, Mary Helene Marmande, Lucy A. Orr and David C. Forbes

Molbank 2025, 2025(3), M2056; https://doi.org/10.3390/M2056 - 30 Aug 2025

Abstract

Overexpression of protein phosphatase 5 (PP5) is linked to tumor cell growth, making it a candidate for small-molecule drug therapy. Since the PP2A domain has been selectively inhibited using functionalized scaffolds that maximize contacts, a similar approach is proposed to work for PP5. [...] Read more.

Overexpression of protein phosphatase 5 (PP5) is linked to tumor cell growth, making it a candidate for small-molecule drug therapy. Since the PP2A domain has been selectively inhibited using functionalized scaffolds that maximize contacts, a similar approach is proposed to work for PP5. As cantharidin’s demethylated cousin, norcantharidin, is a potent but unselective phosphatase inhibitor that can be prepared in just two synthetic steps, the bicyclic scaffold holds promise as an attractive target upon functionalization. Our hypothesis targets PP5 selectivity through derivatives of norcantharidin with functionalized attachments for optimal active-site binding. The methodology offers a promising platform for developing PP5-selective anticancer therapeutics. The approach reported herein exploits anhydride reactivity to yield a carboxylic acid derivative as our next-generation inhibitor of PP5. The methodology offers groundwork for future optimization of norcantharidin-based drug candidates with improved tumor selectivity, potency, and synthetic feasibility. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 332 KB

Open AccessCommunication

Synthesis of Ethyl (S)-3-(1-Methyl-2-Oxo-Cyclohexyl)-2-Oxopropanoate Through Stereoselective Michael Addition

by Domenico C. M. Albanese and Nicoletta Gaggero

Molbank 2025, 2025(3), M2055; https://doi.org/10.3390/M2055 - 28 Aug 2025

Abstract

A practical four-step sequence for the synthesis of α,δ-dioxoesters with high enantiomeric excess was developed. It makes use of a regio- and stereoselective Michael addition of a chiral ketimine to ethyl 2-(phenylthio)-2-propenoate as a key transformation. The synthetic elaboration of the Michael adduct [...] Read more.

A practical four-step sequence for the synthesis of α,δ-dioxoesters with high enantiomeric excess was developed. It makes use of a regio- and stereoselective Michael addition of a chiral ketimine to ethyl 2-(phenylthio)-2-propenoate as a key transformation. The synthetic elaboration of the Michael adduct provides the new ethyl 3-(1-methyl-2-oxo-cyclohexyl)-2-oxopropanoate, bearing a quaternary stereocenter with 95% ee and high yield. Full article

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Graphical abstract

7 pages, 1218 KB

Open AccessCommunication

Synthesis of Novel Spiro-Isoxazolidine Derivatives of 9α-Hydroxyparthenolide

by Mohamed Zaki, Mohammed Loubidi and Sabine Berteina-Raboin

Molbank 2025, 2025(3), M2054; https://doi.org/10.3390/M2054 - 28 Aug 2025

Abstract

The 1,3-dipolar cycloaddition reaction was applied to 9α-hydroxyparthenolide, an important sesquiterpene component of Anvillea radiata that was extracted directly from plant material collected in Morocco. Several new spiro-isoxazolidine derivatives were generated on the B-ring of 9α-hydroxyparthenolide (α-methylene-γ-butyrolactone (1)) by 1,3-dipolar cycloaddition [...] Read more.

The 1,3-dipolar cycloaddition reaction was applied to 9α-hydroxyparthenolide, an important sesquiterpene component of Anvillea radiata that was extracted directly from plant material collected in Morocco. Several new spiro-isoxazolidine derivatives were generated on the B-ring of 9α-hydroxyparthenolide (α-methylene-γ-butyrolactone (1)) by 1,3-dipolar cycloaddition of its exocyclic double bond with various nitrones. These compounds were fully characterized by spectroscopic methods. Full article

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6 pages, 272 KB

Open AccessShort Note

1H,1H,7H-Dodecafluoroheptyl Pentafluorobenzoate

by Sofia S. Kascheeva, Anastasiya V. Lastovka, Andrey S. Vinogradov and Dmitriy A. Parkhomenko

Molbank 2025, 2025(3), M2053; https://doi.org/10.3390/M2053 - 27 Aug 2025

Abstract

Polyfluoroarenes are widely used in organic synthesis because they readily undergo nucleophilic substitution reactions. This reactivity prompted us to report the synthesis and spectroscopic characterization of a new compound, 1H,1H,7H-dodecafluoroheptyl pentafluorobenzoate, obtained via three different approaches starting from pentafluorobenzoic acid and 1H,1H,7H-dodecafluoroheptanol. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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5 pages, 590 KB

Open AccessCommunication

4,4′-Bis(1-(4-nitrophenyl)-2-(2,4,6-trinitrophenyl)hydrazineyl)-1,1′-biphenyl and Its Corresponding Stable Diradical

by Miron T. Caproiu and Petre Ionita

Molbank 2025, 2025(3), M2045; https://doi.org/10.3390/M2045 - 26 Aug 2025

Abstract

Starting with DPPH-diradical, the corresponding dinitro-derivative was obtained in a biphasic system using solid sodium nitrite and 15-crown-5 ether as the nitrating reagents. The new compound was characterized using 1H- and 13C-NMR, IR, and UV-Vis. After undergoing oxidation, a new stable diradical was [...] Read more.

Starting with DPPH-diradical, the corresponding dinitro-derivative was obtained in a biphasic system using solid sodium nitrite and 15-crown-5 ether as the nitrating reagents. The new compound was characterized using 1H- and 13C-NMR, IR, and UV-Vis. After undergoing oxidation, a new stable diradical was obtained, and this was characterized using ESR, IR, and UV-Vis. This process demonstrates that the well-known chemistry based on DPPH can be extended to DPPH-diradical. Full article

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6 pages, 938 KB

Open AccessShort Note

N-[(2H-1,3-benzodioxol-5-yl)methyl]-2-(2,2,2-trichloroacetamido)benzamide

by Plamen Penchev and Dimitar Stoitsov

Molbank 2025, 2025(3), M2052; https://doi.org/10.3390/M2052 - 25 Aug 2025

Abstract

The structure of N-[(2H-1,3-benzodioxol-5-yl)methyl]-2-(2,2,2-trichloroacetamido)benzamide was verified by using a combination of 1D and 2D NMR techniques. Fully assigned data from 1D NMR (¹H, ¹³C and DEPT 135) and 2D NMR (COSY, HMQC, HMBC) spectra was presented for [...] Read more.

The structure of N-[(2H-1,3-benzodioxol-5-yl)methyl]-2-(2,2,2-trichloroacetamido)benzamide was verified by using a combination of 1D and 2D NMR techniques. Fully assigned data from 1D NMR (¹H, ¹³C and DEPT 135) and 2D NMR (COSY, HMQC, HMBC) spectra was presented for the compound. The ¹H NMR spectrum of the ABX spin system in the benzodioxol moiety was simulated to predict the corresponding ⁿJ_HH coupling constants. The spectral assignments for the structure were supported by interpretive library search and HOSE predictions. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 625 KB

Open AccessCommunication

Three Hypoxanthine Derivatives from the Marine Cyanobacterium Okeania hirsuta

by Ryoya Kawabe, Botao Zhang, Ryuichi Watanabe, Hajime Uchida, Masayuki Satake and Hiroshi Nagai

Molbank 2025, 2025(3), M2051; https://doi.org/10.3390/M2051 - 21 Aug 2025

Abstract

Three novel hypoxanthine derivatives (1–3) were obtained from the Okinawan cyanobacterium Okeania hirsuta. The structures of these compounds were elucidated mainly based on the spectroscopic data, including 1D and 2D NMR, as well as high-resolution mass spectrometry. In [...] Read more.

Three novel hypoxanthine derivatives (1–3) were obtained from the Okinawan cyanobacterium Okeania hirsuta. The structures of these compounds were elucidated mainly based on the spectroscopic data, including 1D and 2D NMR, as well as high-resolution mass spectrometry. In particular, the amounts of obtained compounds 2 and 3 were only 200 μg and much less than 50 μg, respectively. Therefore, some carbons signals could not be observed on ¹³C NMR spectra of these compounds. However, the detailed analysis of HSQC and HMBC spectra allowed us to elucidate their structures. For NMR measurements of compound 3, it was found that using an 800 MHz NMR machine equipped with a cryogenic probe and acetic acid-d₄ as a solvent is essential. Compounds (1–3) were N-3′-carbonylbutyl group-connected hypoxanthines. Full article

(This article belongs to the Section Natural Product Chemistry)

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4 pages, 337 KB

Open AccessShort Note

5-[2-(4-Chlorophenyl)-2-oxoethyl]-3-(4-hydroxyphenyl)-2-thioxo-1,3-thiazolidin-4-one

by Nazar Trotsko

Molbank 2025, 2025(3), M2049; https://doi.org/10.3390/M2049 - 20 Aug 2025

Abstract

Rhodanine derivatives, as a subtype of thiazolidin-4-ones, represent an important class of heterocyclic compound known for their broad spectrum of biological activities and practical applications. In this short note, the synthesis of a new compound, 5-[2-(4-chlorophenyl)-2-oxoethyl]-3-(4-hydroxyphenyl)-2-thioxo-1,3-thiazolidin-4-one, is described. The target molecule was synthesized [...] Read more.

Rhodanine derivatives, as a subtype of thiazolidin-4-ones, represent an important class of heterocyclic compound known for their broad spectrum of biological activities and practical applications. In this short note, the synthesis of a new compound, 5-[2-(4-chlorophenyl)-2-oxoethyl]-3-(4-hydroxyphenyl)-2-thioxo-1,3-thiazolidin-4-one, is described. The target molecule was synthesized via a thia-Michael addition followed by cyclocondensation. Its structure was confirmed by ¹H and ¹³C NMR spectroscopy and further supported by 2D NMR studies. Full article

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7 pages, 403 KB

Open AccessCommunication

Synthesis of a New Bioconjugate Steroid Pyridinium Salt Derived from Allopregnanolone Acetate

by Hisami Rodríguez-Matsui, J. Luis Sánchez-Juárez, Vladimir Carranza-Téllez, Joel L. Terán, Jesús Sandoval-Ramirez and Alan Carrasco-Carballo

Molbank 2025, 2025(3), M2050; https://doi.org/10.3390/M2050 - 20 Aug 2025

Abstract

Because allopregnanolone and derivatives represent biologically active molecules, in this letter, we present the synthesis of a new bioconjugate steroid pyridinium salt derived from allopregnanolone in three steps. The key steps involve the formation of the hydrazone intermediate, followed by condensation with bromoacetyl [...] Read more.

Because allopregnanolone and derivatives represent biologically active molecules, in this letter, we present the synthesis of a new bioconjugate steroid pyridinium salt derived from allopregnanolone in three steps. The key steps involve the formation of the hydrazone intermediate, followed by condensation with bromoacetyl bromide and subsequent coupling with pyridine to generate the pyridinium bromide salt. The new bioconjugate steroid pyridinium salt, 4, was fully characterized by proton and carbon nuclear magnetic resonance (¹H and ¹³C NMR) spectroscopy, mass spectrometry (MS), and Fourier transform infrared spectroscopy (FTIR). ¹H-NMR analysis revealed the presence of a dynamic rotameric mixture in a 7:3 ratio of Z/E amide conformers, which were identified by a 2D NOESY experiment. Full article

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7 pages, 612 KB

Open AccessShort Note

4-(1,3-Dioxoisoindolin-2-yl)butyl(2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate

by Zihan Chen, Ka Fai Leong, Carmine Coluccini and Paolo Coghi

Molbank 2025, 2025(3), M2048; https://doi.org/10.3390/M2048 - 19 Aug 2025

Abstract

In this report, we describe the synthesis of a compound derived from the natural compound celastrol, which is connected to a phthalimide moiety via an ester linkage. The compound was fully characterized by proton (¹H), carbon-13 (¹³C), heteronuclear single-quantum [...] Read more.

In this report, we describe the synthesis of a compound derived from the natural compound celastrol, which is connected to a phthalimide moiety via an ester linkage. The compound was fully characterized by proton (¹H), carbon-13 (¹³C), heteronuclear single-quantum coherence (HSQC), and distortionless enhancement by polarization transfer (DEPT) NMR. Ultraviolet–visible spectroscopy (UV-Vis), Fourier-transform infrared (FTIR), and elementary analysis were also performed. Full article

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8 pages, 1233 KB

Open AccessShort Note

5-((3′,5′-Dibromo-[2,2′-bithiophen]-5-yl)methyl)-3-ethyl-2-thioxothiazolidin-4-one∙Br₂ (1:1)

by Enrico Podda, Simone Acca, Maria Carla Aragoni, Vito Lippolis, Anna Pintus, Massimiliano Arca and Giuseppe Sforazzini

Molbank 2025, 2025(3), M2047; https://doi.org/10.3390/M2047 - 14 Aug 2025

Abstract

The reaction of rhodanine vinyl bithiophene (BTR) with molecular dibromine (Br₂) resulted in the formation of compound 1. Single-crystal X-ray diffraction analysis revealed bromination of the terminal thiophenyl ring and the formation of a 1:1 CT “spoke” adduct between the [...] Read more.

The reaction of rhodanine vinyl bithiophene (BTR) with molecular dibromine (Br₂) resulted in the formation of compound 1. Single-crystal X-ray diffraction analysis revealed bromination of the terminal thiophenyl ring and the formation of a 1:1 CT “spoke” adduct between the rhodanine thiocarbonyl group and a neutral dibromine (Br₂) molecule. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 857 KB

Open AccessShort Note

Methyl α-d-Tagatopyranoside

by Yiming Hu, Akihiro Iyoshi, Masakazu Tanaka and Atsushi Ueda

Molbank 2025, 2025(3), M2046; https://doi.org/10.3390/M2046 - 14 Aug 2025

Cited by 1

Abstract

d-Tagatose, classified as a rare sugar, exhibits notable biological activities, including its function as a low-calorie sweetener. The three-dimensional configuration of carbohydrates is crucial for elucidating their functional properties. Numerous studies have reported the X-ray crystallographic structures of d-tagatose and its [...] Read more.

d-Tagatose, classified as a rare sugar, exhibits notable biological activities, including its function as a low-calorie sweetener. The three-dimensional configuration of carbohydrates is crucial for elucidating their functional properties. Numerous studies have reported the X-ray crystallographic structures of d-tagatose and its derivatives bearing a free anomeric hydroxy group. However, there are no reports on the X-ray crystallographic structure of d-tagatosides featuring a glycosidic linkage at the anomeric position. In this study, we synthesized methyl α-d-tagatopyranoside from d-tagatose and successfully determined its X-ray crystallographic structure, revealing its ⁵C₂ conformation. Full article

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6 pages, 640 KB

Open AccessShort Note

Bis(4-((E)-3,5–Diacetoxystyryl)phenyl)nonanedioate

by Claudia Sciacca, Giulia Maria Grasso, Nunzio Cardullo and Vera Muccilli

Molbank 2025, 2025(3), M2044; https://doi.org/10.3390/M2044 - 5 Aug 2025

Abstract

Resveratrol is a natural stilbene known for its wide range of biological activities, including antioxidant, anti-inflammatory, and anti-aging effects. However, its application in cosmetics and dermatology is limited by poor stability and bioavailability. Azelaic acid is a natural carboxylic acid employed in cosmetics [...] Read more.

Resveratrol is a natural stilbene known for its wide range of biological activities, including antioxidant, anti-inflammatory, and anti-aging effects. However, its application in cosmetics and dermatology is limited by poor stability and bioavailability. Azelaic acid is a natural carboxylic acid employed in cosmetics for its tyrosinase inhibition activity and for cutaneous hyperpigmentation disorders. In this work, we report a concise chemoenzymatic procedure for the synthesis of a novel hybrid molecule combining acetylated resveratrol and azelaic acid. This methodology offers a valuable route for the development of new bioactive compounds for potential cosmetic and dermatological applications. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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11 pages, 2689 KB

Open AccessCommunication

Synthesis and Structural Characterization of Manganese(I) Complexes Ligated by 2-Azabutadienes (ArS)₂C=C(H)-N=CPh₂

by Rodolphe Kinghat, Abderrahim Khatyr, Michael Knorr, Yoann Rousselin and Marek M. Kubicki

Molbank 2025, 2025(3), M2042; https://doi.org/10.3390/M2042 - 28 Jul 2025

Cited by 1

Abstract

The thioether-functionalized 2-azabutadienes (ArS)₂C=C(H)-N=CPh₂ (L1 Ar = Ph, L2 Ar = p-Tol) ligate to [Mn(CO)₅Br] to form the octahedral five-membered S, N-chelate complexes fac-[MnBr(CO)₃{(ArS)₂C=C(H)-N=CPh₂] (1 Ar [...] Read more.

The thioether-functionalized 2-azabutadienes (ArS)₂C=C(H)-N=CPh₂ (L1 Ar = Ph, L2 Ar = p-Tol) ligate to [Mn(CO)₅Br] to form the octahedral five-membered S, N-chelate complexes fac-[MnBr(CO)₃{(ArS)₂C=C(H)-N=CPh₂] (1 Ar = Ph; 2 Ar = p-Tol), whose crystal structures have been solved by X-ray diffraction. Complex 1 crystallizes in the non-centrosymmetric orthorhombic space group P2₁2₁2₁, whereas 2 crystallizes in the triclinic space group P

\bar{1}

. The secondary interactions occurring in the packing have also been assessed by an Atoms in Molecules (AIM) topological analysis. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 790 KB

Open AccessShort Note

6-Amino-4-phenylpyrrolo[2,3-c][1,2,6]thiadiazine-5-carbonitrile

by Andreas S. Kalogirou, Andreas Kourtellaris and Panayiotis A. Koutentis

Molbank 2025, 2025(3), M2043; https://doi.org/10.3390/M2043 - 28 Jul 2025

Abstract

The reaction of 2-(3-chloro-5-phenyl-4H-1,2,6-thiadiazin-4-ylidene)malononitrile with ammonia in anhydrous THF, at ca. 20 °C, for 24 h, gave 6-amino-4-phenylpyrrolo[2,3-c][1,2,6]thiadiazine-5-carbonitrile in 95% yield. The product was characterized by ¹H and ¹³C NMR, SC-XRD, MALDI-TOF mass spectrometry, FTIR, and UV-vis [...] Read more.

The reaction of 2-(3-chloro-5-phenyl-4H-1,2,6-thiadiazin-4-ylidene)malononitrile with ammonia in anhydrous THF, at ca. 20 °C, for 24 h, gave 6-amino-4-phenylpyrrolo[2,3-c][1,2,6]thiadiazine-5-carbonitrile in 95% yield. The product was characterized by ¹H and ¹³C NMR, SC-XRD, MALDI-TOF mass spectrometry, FTIR, and UV-vis spectroscopy. Intermolecular hydrogen bonding interactions were observed in the solid state between the C≡N and N-H groups of adjacent molecules. Full article

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7 pages, 421 KB

Open AccessShort Note

1,3,4,5-Tetra-O-benzoyl-α-d-tagatopyranose

by Yiming Hu, Akihiro Iyoshi, Yui Makura, Masakazu Tanaka and Atsushi Ueda

Molbank 2025, 2025(3), M2041; https://doi.org/10.3390/M2041 - 22 Jul 2025

Cited by 2

Abstract

d-Tagatose, a rare sugar, is recognized as a low-calorie sweetener, used in daily life. Although d-tagatose exhibits intriguing biological activities, the synthesis of its derivatives has rarely been reported. In this study, we developed a method for synthesizing 1,3,4,5-tetra-O-benzoyl-α- [...] Read more.

d-Tagatose, a rare sugar, is recognized as a low-calorie sweetener, used in daily life. Although d-tagatose exhibits intriguing biological activities, the synthesis of its derivatives has rarely been reported. In this study, we developed a method for synthesizing 1,3,4,5-tetra-O-benzoyl-α-d-tagatopyranose through the regioselective benzoylation of d-tagatose in a single step, achieving an 88% yield on a gram scale. Additionally, 1,2,3,4,5-penta-O-benzoyl-α-d-tagatopyranose and 1,2,3,4,6-penta-O-benzoyl-α-d-tagatofuranose were synthesized in 50% yield as a 7:1 mixture. The structures of the three new benzoylated d-tagatose derivatives were confirmed by ¹H, ¹³C NMR, 2D NMR, FT-IR, and HRMS analyses. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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7 pages, 636 KB

Open AccessShort Note

Benzyl-N-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]carbamate

by Lucrezia Spinelli, Matteo Mori and Laura Fumagalli

Molbank 2025, 2025(3), M2040; https://doi.org/10.3390/M2040 - 21 Jul 2025

Abstract

Heterocycles—cyclic compounds containing at least one non-carbon heteroatom (e.g., N, O, S)—are fundamental in medicinal chemistry due to their influence on a drug’s physicochemical and biological properties. They improve solubility, bioavailability, and facilitate molecular recognition through their electronic and hydrogen-bonding features. These properties [...] Read more.

Heterocycles—cyclic compounds containing at least one non-carbon heteroatom (e.g., N, O, S)—are fundamental in medicinal chemistry due to their influence on a drug’s physicochemical and biological properties. They improve solubility, bioavailability, and facilitate molecular recognition through their electronic and hydrogen-bonding features. These properties make them indispensable in drug design. This study focuses on the synthesis of a key heterocyclic intermediate: benzyl-N-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]carbamate. This molecule incorporates a thiazole ring, known for its rigidity and electronic properties, that enhances target interactions. The 2-position bears a Cbz-protected amine, enabling orthogonal deprotection, while the 4-position features a hydroxyethyl side chain, providing a handle for further chemical modifications via nucleophilic substitution. Herein, we report the successful synthesis of this intermediate along with its full ¹H and ¹³C NMR spectra, melting point, and crystal structure, confirming its identity and purity. Full article

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16 pages, 1696 KB

Open AccessCommunication

Synthesis and Characterization of Amide-Based Cyclotriphosphazene Derivatives with Alkoxy Terminal Groups

by Khairunnisa Abdul Rahim and Zuhair Jamain

Molbank 2025, 2025(3), M2039; https://doi.org/10.3390/M2039 - 21 Jul 2025

Abstract

A series of new amide-based cyclotriphosphazene molecules consisting of different terminal groups (heptyl, decyl, and tetradecyl) at the periphery was successfully synthesized and characterized. The reaction began with the alkylation of methyl-4-hydroxybenzoate with 1-bromoheptane, 1-bromodecane, and 1-bromotetradecane, which was followed by reduction with [...] Read more.

A series of new amide-based cyclotriphosphazene molecules consisting of different terminal groups (heptyl, decyl, and tetradecyl) at the periphery was successfully synthesized and characterized. The reaction began with the alkylation of methyl-4-hydroxybenzoate with 1-bromoheptane, 1-bromodecane, and 1-bromotetradecane, which was followed by reduction with potassium hydroxide to form a series of benzoic acid intermediates (1a–c). These intermediates underwent a reaction with thionyl chloride, followed by a reaction with 4-nitroaniline and triethylamine, to form para-substituted amides (2a–c). Further reduction of intermediates 2a–c with sodium sulfide hydrate produced the anilines 3a–c. Another reaction of hexachlorocyclotriphosphazene (HCCP) with methyl-4-hydroxybenzoate yielded intermediate 4, which was then reduced with sodium hydroxide to form intermediate 5. Finally, chlorination of intermediate 5 with thionyl chloride, followed by a reaction with the aniline derivatives (3a–c), formed the hexasubstituted cyclotriphosphazene compounds 6a–c, with two amide linkages. The structures of these compounds were confirmed using Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy and CHN elemental analysis. Full article

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