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Keywords = 1,4-enedione derivatives

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21 pages, 3145 KB  
Article
Dipolarophile-Controlled Regioselective 1,3-Dipolar Cycloaddition: A Switchable Divergent Access to Functionalized N-Fused Pyrrolidinyl Spirooxindoles
by Yongchao Wang, Lijun Yan, Yuxin Yan, Sujin Li, Hongying Lu, Jia Liu and Jianwei Dong
Int. J. Mol. Sci. 2023, 24(4), 3771; https://doi.org/10.3390/ijms24043771 - 13 Feb 2023
Cited by 12 | Viewed by 3209
Abstract
N-fused pyrrolidinyl spirooxindole belongs to a class of privileged heterocyclic scaffolds and is prevalent in natural alkaloids and synthetic pharmaceutical molecules. To realize the switchable synthesis of divergent N-fused pyrrolidinyl spirooxindoles for further biological activity evaluation via a substrate-controlled strategy, a [...] Read more.
N-fused pyrrolidinyl spirooxindole belongs to a class of privileged heterocyclic scaffolds and is prevalent in natural alkaloids and synthetic pharmaceutical molecules. To realize the switchable synthesis of divergent N-fused pyrrolidinyl spirooxindoles for further biological activity evaluation via a substrate-controlled strategy, a chemically sustainable, catalysis-free, and dipolarophile-controlled three-component 1,3-dipolar cycloaddition of isatin-derived azomethine ylides with diverse dipolarophiles is described in this work. A total of 40 functionalized N-fused pyrrolidinyl spirooxindoles were synthesized in 76–95% yields with excellent diastereoselectivities (up to >99:1 dr). The scaffolds of these products can be well-controlled by employing different 1,4-enedione derivatives as dipolarophiles in EtOH at room temperature. This study provides an efficient strategy to afford a spectrum of natural-like and potentially bioactive N-fused pyrrolidinyl spirooxindoles. Full article
(This article belongs to the Section Biochemistry)
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19 pages, 2424 KB  
Article
2-Aryl-6-Polyfluoroalkyl-4-Pyrones as Promising RF-Building-Blocks: Synthesis and Application for Construction of Fluorinated Azaheterocycles
by Sergey A. Usachev, Diana I. Nigamatova, Daria K. Mysik, Nikita A. Naumov, Dmitrii L. Obydennov and Vyacheslav Y. Sosnovskikh
Molecules 2021, 26(15), 4415; https://doi.org/10.3390/molecules26154415 - 21 Jul 2021
Cited by 12 | Viewed by 3766
Abstract
A convenient and general method for the direct synthesis of 2-aryl-6-(trifluoromethyl)-4-pyrones and 2-aryl-5-bromo-6-(trifluoromethyl)-4-pyrones has been developed on the basis of one-pot oxidative cyclization of (E)-6-aryl-1,1,1-trifluorohex-5-ene-2,4-diones via a bromination/dehydrobromination approach. This strategy was also applied for the preparation of 2-phenyl-6-polyfluoroalkyl-4-pyrones and their [...] Read more.
A convenient and general method for the direct synthesis of 2-aryl-6-(trifluoromethyl)-4-pyrones and 2-aryl-5-bromo-6-(trifluoromethyl)-4-pyrones has been developed on the basis of one-pot oxidative cyclization of (E)-6-aryl-1,1,1-trifluorohex-5-ene-2,4-diones via a bromination/dehydrobromination approach. This strategy was also applied for the preparation of 2-phenyl-6-polyfluoroalkyl-4-pyrones and their 5-bromo derivatives. Conditions of chemoselective enediones bromination were found and the key intermediates of the cyclization of bromo-derivatives to 4-pyrones were characterized. Synthetic application of the prepared 4-pyrones has been demonstrated for the construction of biologically important CF3-bearing azaheterocycles, such as pyrazoles, pyridones, and triazoles. Full article
(This article belongs to the Special Issue Organofluorine Chemistry and Beyond)
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10 pages, 770 KB  
Article
Nine New Gingerols from the Rhizoma of Zingiber officinale and Their Cytotoxic Activities
by Zezhi Li, Yanzhi Wang, MeiLing Gao, Wanhua Cui, Mengnan Zeng, Yongxian Cheng and Juan Li
Molecules 2018, 23(2), 315; https://doi.org/10.3390/molecules23020315 - 2 Feb 2018
Cited by 25 | Viewed by 5709
Abstract
Nine new gingerols, including three 6-oxo-shogaol derivatives [(Z)-6-oxo-[6]-shogaol (1), (Z)-6-oxo-[8]-shogaol (2), (Z)-6-oxo-[10]-shogaol (3)], one 6-oxoparadol derivative [6-oxo-[6]-paradol (4)], one isoshogaol derivative [(E)-[4]-isoshogaol (5)], and four [...] Read more.
Nine new gingerols, including three 6-oxo-shogaol derivatives [(Z)-6-oxo-[6]-shogaol (1), (Z)-6-oxo-[8]-shogaol (2), (Z)-6-oxo-[10]-shogaol (3)], one 6-oxoparadol derivative [6-oxo-[6]-paradol (4)], one isoshogaol derivative [(E)-[4]-isoshogaol (5)], and four paradoldiene derivatives [(4E,6Z)-[4]-paradoldiene (8), (4E,6E)-[6]-paradoldiene (9), (4E,6E)-[8]-paradoldiene (10), (4E,6Z)-[8]-paradoldiene (11)], together with eight known analogues, were isolated from the rhizoma of Zingiber officinale. Their structures were elucidated on the basis of spectroscopic data. It was noted that the isolation of 6-oxo-shogaol derivatives represents the first report of gingerols containing one 1,4-enedione motif. Their structures were elucidated on the basis of spectroscopic and HRESIMS data. All the new compounds were evaluated for their cytotoxic activities against human cancer cells (MCF-7, HepG-2, KYSE-150). Full article
(This article belongs to the Special Issue Chemical Biology of Sterols, Triterpenoids and Other Natural Products: A Themed Issue in Honor of Professor W. David Nes on the Occasion of His 65th Birthday)
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13 pages, 253 KB  
Article
A Highly Efficient Regioselective Addition of Acetylides to Enediones Based on Steric Effects
by Xiaoqiang Han, Chuan Wan, Dongyan Yang, Xiaoyong Yuan, Shijie Du, Yumei Xiao and Zhaohai Qin
Molecules 2013, 18(9), 10776-10788; https://doi.org/10.3390/molecules180910776 - 3 Sep 2013
Cited by 5 | Viewed by 4677
Abstract
A simple and efficient strategy for the synthesis of 1-ethynylcyclohex-2-enol derivatives was developed utilizing regioselective addition of acetylides to enediones based on steric effects. Further investigation of the substrate scope of enediones indicated that all the addition reactions ocurred in good yield. Full article
(This article belongs to the Section Organic Chemistry)
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