Synthesis of the First Representatives of Thieno[3,2-c][1,7]naphthyridine Derivatives Based on 3-Amino-6-methyl-4-(2-thienyl) pyridin-2(1H)-one

Кулаков, И. В.; Matsukevich, Mariya V.; Levin, Maxim L.; Паламарчук, Ирина В.; Сейлханов, Т. М.; Fisyuk, A. S.

doi:10.1055/s-0037-1610445

Cited by 11 publications

(4 citation statements)

References 12 publications

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“…When heating the latter with aromatic aldehydes in polyphosphoric acid, the Pictet–Spengler reaction took place, and the intermediate compounds were oxidized by atmospheric oxygen to form the previously unknown benzo[ c ][1,7]naphthyridine-4(3 H )-ones (Scheme ). Similarly, thieno[3,2- c ][1,7]naphthyridine-6(7 H )-ones have been obtained . The disadvantage of this method is the severe reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones

et al. 2020

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In this work, we describe the development of the rearrangement for 7-aryl-substituted oxazolo [5,4-b]pyridines treated with aluminum chloride into synthetically hard-to-reach benzo [c][1,7]naphthyridinones. The discovered rearrangement is applied to a variety of electron-rich (hetero)arene substrates. It offers the advantages of mild conditions (90 °C temperature), fast reaction rates (<4 h), compatibility with air moisture, and the use of inexpensive commercial reagents. The proposed reaction mechanism and key elementary reaction acts were studied in detail using quantum chemical calculations. The photophysical properties of the synthesized compounds were studied by steady-state UV−vis spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones

et al. 2020

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“…We also developed and optimized a general one-pot method for the preparation of previously unavailable 6-arylbenzo(thieno)[c] [1,7]naphthyridin-4(3H)ones, which were not described in the literature. The method is based on the Pict-Spengler reaction of 3-amino-4arylpyridine-2(1H)-ones with aromatic aldehydes in acidic media (polyphosphoric acid, 80% Н 3 РО 4 ) [26,27].…”

Section: Doi: 101134/s1070363222090110mentioning

confidence: 99%

Synthesis, Molecular Docking, and Hemorheological Activity of New 4-(Thien-2-yl)-3-aminopyridine-2(1H)-one Derivatives

Паламарчук

Shulgau²,

Sergazy³

et al. 2022

Russ J Gen Chem

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On the basis of 4-(thien-2-yl)-3-aminopyridine-2(1H)-one, the corresponding chloroacetamide and condensed 1H-pyrido[2,3-b][1,4]oxazine-2(3H)-one were synthesized by the reaction of acylation with chloroacetyl chloride. Thioureide derivatives of 3-aminopyridine-2(1H)-one were obtained by reactions with a number of isothiocyanates. It was shown that the carbamothionylmethacrylamide derivative cyclizes rather easily into substituted 1,3-thiazine. Molecular docking of synthesized derivatives for antithrombotic activity was carried out, which showed that the presence of a thiourea fragment in the pyridone core leads to an increase in affinity for the selected protein. The hemorheological study of the compounds using the in vitro model of the increased blood viscosity syndrome also showed activity at the level of the reference drug pentoxifylline.

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“…as a privileged structural motif in organic chemistry. [14][15][16][17] Among them, the 1,8-naphthyridines nucleus constitute the main core of diverse pharmaceutical drugs such as Gemi oxacin, Vosaroxin, Enoxacin, Trova oxacin mesylate, Nalidixic acid, etc., as demonstrated in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

A novel pillar-layered MOF with the urea linkers: A capable catalyst for the synthesis of new 1,8-naphthyridines via the anomeric-based oxidation

Beiranvand,

Habibi,

Khodakarami

2024

Preprint

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Metal-based catalysts play an essential role in organic chemistry and the chemical industry. In this research, a pillar-layered metal-organic framework (MOF) with the urea linkers, namely Basu-HDI, as a novel and efficient heterogeneous catalyst was designed and successfully synthesized. Various techniques such as FT-IR, EDX, elemental mapping, SEM, XRD, BET, and TGA/DTA studied its structure and morphology. Then, we investigated the synthesis of new 1,8-naphthy-ridines utilizing Basu-HDI in mild conditions via a one‐pot three‐component tandem Knoevenagel/ Michael/cyclization/anomeric-based oxidation reaction. Final products were achieved by anomeric-based oxidation without employing an oxidation agent. Remarkably, this tandem process gave a good range of new 1,8-naphthyridines with high yields in a short reaction time. The pure products were confirmed by FT-IR, 1H NMR, 13C NMR, and mass spectrometry techniques. Moreover, the introduced catalyst showed good efficiency and stability and can be reused four times without significantly reducing efficiency.

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Synthesis of the First Representatives of Thieno[3,2-c][1,7]naphthyridine Derivatives Based on 3-Amino-6-methyl-4-(2-thienyl) pyridin-2(1H)-one

Cited by 11 publications

References 12 publications

Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones

Rearrangement of 7-Aryloxazolo[5,4-b]pyridines to Benzo[c][1,7]naphthyridine-4(3H)-ones and Thieno[3,2-c][1,7]naphthyridine-6(7H)-ones

Synthesis, Molecular Docking, and Hemorheological Activity of New 4-(Thien-2-yl)-3-aminopyridine-2(1H)-one Derivatives

A novel pillar-layered MOF with the urea linkers: A capable catalyst for the synthesis of new 1,8-naphthyridines via the anomeric-based oxidation

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