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- Synthesis and Molecular Docking Studies of N,N-Dimethyl
Arylpyranopyrimidinedione Derivatives
Authors: Prabhakaran; Srinivasan, Velmathi, Sivan
Pages: 1 - 6
Abstract: The synthesis of N,N-dimethyl arylpyranopyrimidinedione derivatives from aromatic aldehydes, N-methyl-1-(methylthio)-2-nitroethamine (NMSM) and 1,3-dimethyl barbituric acid, in the presence of piperidine as a catalyst, is reported. The reaction mechanism involves a Knoevenagel condensation, followed by Michael addition and intramolecular O-cyclization reaction sequence. The synthesized compounds were docked with human kinesin Eg5 protein to calculate binding energy, inhibition constant and H-bond interaction. All the compounds show good binding affinity towards the protein, with significant docking score.
Citation: SynOpen 2022; 06: 1-6
PubDate: 2022-01-10T00:00:00+0100
DOI: 10.1055/s-0040-1719869
Issue No: Vol. 06, No. 01 (2022)
- Synthesis of [1,4]Oxathiepino[5,6-b]quinolines via Base-Mediated
Intramolecular Hydroalkoxylation
Authors: Tonekaboni; Maryam-Sadat, Tanbakouchian, Zahra, Majedi, Soma, Shiri, Morteza
Pages: 7 - 10
Abstract: A base-mediated intramolecular hydroalkoxylation that was used to prepare a series of seven-membered S,O-heterocycles is described. 2-Thiopropargyl-3-hydroxymethyl quinolines were prepared starting from 2-mercaptoquinoline-3-carbaldehydes, via S-propargylation and reduction of a formyl group. Interestingly, 2-mercaptopropargyl-3-hydroxymethyl quinolines were converted into the corresponding oxathiepinoquinolines in the presence of t-BuOK. It is proposed that the S-propargyl moiety, in the presence of base, is converted into its allenyl isomer; subsequent addition of a hydroxyl group to the terminal double bond yields the 3-methyl-5H-[1,4]oxathiepino[5,6-b]quinoline in good to high yield. Notably, the procedure is adaptable to the conversion of N-propargyl indole-2-methanol into the corresponding intramolecular hydroalkoxylation product.
Citation: SynOpen 2022; 06: 7-10
PubDate: 2022-01-10T00:00:00+0100
DOI: 10.1055/s-0040-1719868
Issue No: Vol. 06, No. 01 (2022)
- Efficient Synthesis of Isoquinoline Derivatives through Sequential
Cyclization–Deoxygenation Reaction of 2-Alkynylbenzaldoximes
Authors: Ayoubi; Mojtaba, Nikbakht, Ali, Amiri, Kamran, Abbasi Kejani, Alireza, Zahedian Tejeneki, Hossein, Balalaie, Saeed
Pages: 11 - 15
Abstract: We describe a novel, simple, robust, and efficient cyclization/deoxygenation approach for the synthesis of functionalized isoquinoline derivatives. Over the course of continued studies on o-alkynylbenzaldoxime cyclization reactions, the formation of cyclic nitrones through 6-endo-dig cyclization was achieved using silver triflate or bromine as an electrophile, and subsequently, the deoxygenation process was carried out in the presence of CS2 in good to high yields.
Citation: SynOpen 2022; 06: 11-15
PubDate: 2022-01-13T00:00:00+0100
DOI: 10.1055/s-0040-1719870
Issue No: Vol. 06, No. 01 (2022)
- Indium-Mediated Reformatsky Reaction of Iododifluoro Ketones with
Aldehydes: Preparation of α,α-Difluoro-β-hydroxyketone Derivatives in
Water
Authors: Li; Zhongyuan, Huang, Jinwen, Ni, Zhuang, Sun, Ran, Nie, Hui, Tang, Hui, Song, Lixing, Wu, Fanhong
Pages: 19 - 30
Abstract: Indium can efficiently mediate the Reformatsky reaction of iododifluoroacetylketones with aldehydes to afford the corresponding α,α-difluoro-β-hydroxyketones in high yield in pure water This reaction has excellent substrate suitability and functional group selectivity and provides an efficient approach for the synthesis of bioactive molecules containing the α,α-difluoro-β-hydroxyketone pharmacophore.
Citation: SynOpen 2022; 06: 19-30
PubDate: 2022-01-31T00:00:00+0100
DOI: 10.1055/s-0040-1719888
Issue No: Vol. 06, No. 01 (2022)
- Hydrogen-Bonded Xanthones as Potential UV Absorbers: The Synthesis of
Xanthones from Bio-Renewable Cardanol Utilizing a Ceric Ammonium Sulfate
(CAS)-Mediated Oxidation Reaction
Authors: Jagot; Fatema, Minnie, Izak, Rahman, Aliyaah, Ntsimango, Songeziwe, Ngwira, Kennedy J., de Koning, Charles B.
Pages: 58 - 66
Abstract: The synthesis of hydrogen-bonded xanthones by using biorenewable hydrogenated cardanol (3-pentadecylphenol) is described. Hydrogenated cardanol was initially converted into various hydroxybenzophenones. These benzophenones were converted into xanthones by utilizing an oxidative ceric ammonium sulfate-mediated reaction. A subsequent ruthenium-mediated late-stage oxidation of the xanthones provided hydrogen-bonded xanthones, which displayed good UVA and UVB absorbing properties.
Citation: SynOpen 2022; 06: 58-66
PubDate: 2022-02-24T00:00:00+0100
DOI: 10.1055/s-0040-1719903
Issue No: Vol. 06, No. 01 (2022)
- Tethered Rh(III)-N-(p-Tolylsulfonyl)-1,2-Diphenylethylene-1,2-Diamine
Complexes: Efficient Catalysts for Asymmetric Transfer HydrogenationSynOpen 2022; 06: 75-79
DOI: 10.1055/s-0040-1719914
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Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, Germany
Artikel in Thieme eJournals:
Inhaltsverzeichnis Abstract open access Volltext
SynOpen 2022; 06: 75-792022-03-24T00:00:00+0100
Issue No: Vol. 06, No. 01 (2022)
- Asymmetric Sequential Michael Addition and Cyclization Reactions of
2-(2-Nitrovinyl)phenols Catalyzed by Bifunctional Amino-Squaramides
Authors: Veverková; Eva, Molnosiová, Pavlína, Šebesta, Radovan
Pages: 278 - 284
Abstract: In this work, we describe the Michael addition–cyclization reaction of 2-(2-nitrovinyl)phenol with two different reactive Michael donors, which lead to chiral benzopyran derivatives. Specifically, bifunctional amino-squaramides with one or two chiral units in the side chains were evaluated as catalysts in these transformations. Furthermore, the utility of selected green solvents as reaction media for these processes was also tested. The best result was achieved with methyl-cyclopentanone-2-carboxylate as the Michael donor in ethyl (–)-l-lactate with quinine-based amino-squaramide as catalyst (yield 72%, dr >99:1, ee 99%).
Citation: SynOpen 2021; 05: 278-284
PubDate: 2021-10-05T00:00:00+01:00
DOI: 10.1055/s-0040-1719843
Issue No: Vol. 05, No. 04 (2021)
- Oxidative Annulation of Diphenylpropanamides via In Situ Hypervalent
Iodine-Promoted Intramolecular C–N/C–O Bond Formation
Authors: Liang; Zhi-Peng, Yu, Ying-Xin, Sun, Yuan-Yuan, Wang, Yang, Wu, Zheng-Guang
Pages: 327 - 334
Abstract: An aryl iodide catalyzed intramolecular oxidative transformation of diphenylpropanamide derivatives is described that can readily afford the C–N/C–O coupling products in a single step. The speed of the 1,3-aryl iodide migration process determines the diversity of target compound generation in this reaction. This straightforward approach can be performed with the use of inexpensive and readily available catalyst, transition-metal-free, mild conditions and good functional group tolerance.
Citation: SynOpen 2021; 05: 327-334
PubDate: 2021-12-21T00:00:00+0100
DOI: 10.1055/s-0040-1719861
Issue No: Vol. 05, No. 04 (2021)
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