Tetrahedron Letters最新文献

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A convenient ammonium chloride facilitated mild and efficient synthesis of Benzazepinoindole derivatives through a Pictet-Spengler reaction*

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-19 DOI: 10.1016/j.tetlet.2025.155529

Chibisree Elanchezhian , Diksha Bansal , Pooja Sivaganesan , Gokulprasanth Nataraj , Mrinal Kanti Das , Saikat Chaudhuri

Benzazepinoindoles are a promising class of compounds in the growing field of heterocyclic chemistry due to their intriguing pharmacological properties. The tetrahydro-benzazepinoindole scaffold, in particular, holds great promise as a versatile framework for drug discovery, especially in the development of antiproliferative and anti-inflammatory agents. In present work, we proposed the synthesis of tetrahydro-benzazepinoindoles starting from alkylated indole and benzaldehyde derivatives using NH₄Cl, and methanol as solvent. This approach is designed to achieve high efficiency and good to excellent yields, while accommodating diverse functional groups to enhance structural diversity. The scalability of this method was demonstrated through successful gram-scale reactions, highlighting its utility in practical applications. The synthesized compounds were characterized using advanced techniques, including ¹H NMR, ¹³C NMR, ¹⁹F NMR, DEPT-135, IR and mass spectrometry, confirming their structural integrity. This work provides a streamlined and reliable strategy for the synthesis of tetrahydro-benzazepinoindoles, contributing to advancements in synthetic methodology and paving the way for the development of novel bioactive molecules with significant therapeutic potential.

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引用次数: 0

Visible-light-induced aerobic C-3 thiocyanation of indoles using carbon dots as photoredox catalyst 利用碳点作为光氧化催化剂，在可见光诱导下进行吲哚的有氧 C-3 硫氰化反应

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-15 DOI: 10.1016/j.tetlet.2025.155545

Pritesh Khobrekar , Sandesh Bugde

In this work, we demonstrate the use of rose-bengal derived carbon dots for C-3 thiocyanation of indoles. These carbon dots serve as an non-toxic, biocompatible and environmentally friendly catalysts for the C-3 thiocyanation reaction. To our best knowledge, this is the first report to use rose-bengal derived carbon dots for C-3 thiocyanation of indoles. The yield of the synthesized derivatives of indoles were found to be good to excellent in the range of 33 % to 84 %.

引用次数: 0

Synthesis and Structural Confirmation of PyHOPO and its Applicability in Racemization Reduction in Solid-Phase Peptide Synthesis

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-10 DOI: 10.1016/j.tetlet.2025.155520

Kwazi Masuku , Anamika Sharma , Sikabwe Noki , Sizwe Zamisa , Ayman El-Faham , Beatriz G. de la Torre , Fernando Albericio

In the current work, PyHOPO was synthesized and well characterized by single ray XRD. The crystal structure unambiguously confirmed the presence of a P-O-N bond rather than a P-O-C bond. The conversion of HOPO to PyHOPO elongates the NO bond length thereby changing the electron density distribution, as evidenced by electrostatic mapping. This highlights the phosphorus atom's electron-donating nature toward the HOPO moiety. PyHOPO was used to prepare pentapeptide H-Tyr-Ser-Ser-Phe-Leu-NH₂. PyHOPO was then evaluated for racemization study. Racemization was studied in the case of Ser, His and Cys upon incorporation in a tripeptide (Gly-X-Phe-NH₂; where X = Ser, His, Cys). For the study, it was found that there was no racemization in all the three cases when PyHOPO was used as coupling reagent.

引用次数: 0

Construction of Amidines via palladium-catalyzed three-component reaction of Arylacetylenes, t-Butylisonitrile and O-benzoyl Hydroxylamines

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-06 DOI: 10.1016/j.tetlet.2025.155534

Jianquan Hong, Feng Zheng, Xiaoyu Wang, Mingyu Ma, Yupeng Yang, Lianguang Huo, Shuai Huang, Changge Zheng

A palladium-catalyzed three-component reaction between arylacetylenes, t-butylisonitrile and O-benzoyl hydroxylamines has been developed. This transformation provides an efficient approach to access various alkynylamidine derivatives via tandem CH activation/insertion/amidination procedure.

引用次数: 0

Synthesis of spiroisoxazoline oxindoles by base-promoted annulation of oxime esters and isatins

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-06 DOI: 10.1016/j.tetlet.2025.155506

Si-Wei Chen , Xu-Hua Hu , Ling Wu , Chun-Bao Miao , Xun-Xiang Guo

A base-promoted annulation reaction of oxime esters and isatins has been developed for the facile and rapid synthesis of spiroisoxazoline oxindoles. This method demonstrates high efficiency, enabling the synthesis of a variety of spiroisoxazoline oxindoles with good to high yields under simple and mild conditions.

引用次数: 0

Synthesis of Ortho-nitrochalcones by solvent-free grinding method: Facilitating the synthesis of 2,3-Disubstituted Quinoline N-oxides via bimolecular reaction

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-05 DOI: 10.1016/j.tetlet.2025.155533

Sai Wang , Wangyuan Zhan , Deguang Huang , XiaoFeng Zhang

A method for the synthesis of 2,3-disubstituted quinoline N-oxides, ortho-nitrochalcones, and their derivatives is reported. Through mortar-pestle grinding under solvent-free conditions, a series of ortho-nitrochalcone derivatives, naphthalenone derivatives, and indenone derivatives were obtained in good to excellent yields. Additionally, by using ortho-nitrochalcones and their derivatives along with 2-nitrobenzaldehyde as starting materials, in the presence of a specific ratio of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and sodium hydroxide (NaOH), and with 1,2-diphenylhydrazine involved, 2,3-disubstituted quinoline N-oxides were synthesized through a bimolecular reaction. This synthetic approach features metal-free catalysis, employs inexpensive and easily accessible raw materials, and operates under mild reaction conditions, thereby enriching the research domain of organic synthesis.

引用次数: 0

Greener synthesis of Pyrroloacridine-1(2H)-one and 1,8-Dioxodecahydroacridine derivatives: Ascorbic acid mediated OrganocatalyticApproach

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155518

Saptadwipa Bhattacharjee, Puja Basak, Pranab Ghosh

A simple, one-pot multi component synthetic route employing ascorbic acid is reported for synthesising pyrrolo[2,3,4-kl]acridin and 1,8-dioxodecahydroacridine derivatives under solvent free condition. This method offers advantages such as moderate conditions, ease of operation, environmental friendliness, and organocatalyst. The suggested technique features green reaction conditions, a broad substrate scope, operational simplicity, an eco-efficient catalyst, the production of CN bonds, and excellent product yields.

引用次数: 0

Nitration of deactivated aromatic compounds using Lithium nitrate

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155515

Weihao Ma , J. Tyler McBride , Robert S. Phillips

Nitroarenes are critically important in medicinal chemistry, material science, and the chemical industry. In this paper, we introduce a new strategy for the electrophilic nitration of deactivated aromatic compounds, utilizing lithium nitrate (LiNO₃) in the presence of sulfuric acid in trifluoroacetic acid. This method has demonstrated moderate to excellent yield. Mild reaction conditions and easy workup make the synthesis of nitro compounds both practical and commercially feasible.

引用次数: 0

Synthesis of bis-sulfonium lipids and their antibacterial ability

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155528

Chengcai Liu , Xiaodong Zhou , Xinrui Bi , Peiyu Chen , Wanning Li , Jing Li

Gemini cationic surfactants have great advantages as antibacterial agents. Herein, a group of bis-sulfonium lipids was synthesized and their antibacterial activities were investigated on Gram-negative and Gram-positive bacterial stains. The activity of bis-sulfonium lipids was related to the hydrophobic substitution. When each of the sulfonium contained one long alkyl chain and the spacer was short, the gemini salt exhibited strong inhibition. The compound with benzyl, decyl and pentylene spacer exhibited the broad antibacterial activity, and was more sensitive on Gram-negative than commercial quaternary ammonium salts. The mechanism study showed that increasing cell membrane permeability and disrupting the cell membrane are important pathways for inhibiting bacteria.

引用次数: 0

One-pot synthesis and anti-proliferative activity of hindered 5-amino-1-alkylimidazole-4-carboxamides

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters

Pub Date : 2025-03-03 DOI: 10.1016/j.tetlet.2025.155517

Yamei Zhang , Zijuan Yang , Yong Xie , Yeming Wang

One-pot procedure was developed for the synthesis of hindered 5-amino-1-alkylimidazole-4-carboxamides by using bulky alkyl amines with trimethyl orthoformate and 2-amino-2-cyanoacetamide. Under optimized conditions, the reactivity of a series of steric hindrance substrates was examined, producing the corresponding hindered 5-amino-1-alkylimidazole-4-carboxamides with good to excellent yields. This synthetic method has several advantages including metal- and additive-free, short reaction time and wide substrate scope with good to excellent yields. Besides, 5-amino-1-(4-fluorobenzyl)-1H-imidazole-4-carboxamide (3j) exhibited potent antiproliferative activity against A375(B-RAF^V600E) cells as a novel anti-tumor agent, and the molecular docking model showed that carboxamide moiety of 3j was a key active functional group, forming two hydrogen bonds with Lys483 and Phe595，which was similar to the function of sulfonamide of vemurafenib. To our delight, the imidazole scaffold of 3j formed a novel hydrogen bond with Asp594, and there was π…π interaction between the phenyl group of 3j and Phe583, which were different from binding mode of vemurafenib. The binding mode between 3j and B-RAF^V600E kinase provided a reasonable explanation for 3j as a potential B-RAF^V600E kinase inhibitor.

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