Convenient synthesis of trifluoromethylated 2-pyrrolidone and 2-pyrrolone derivatives

Sibgatulin, Dmitriy A.; Kostyuk, Alexander; Volochnyuk, Dmitriy M.; Русанов, Эдуард Б.; Chernega, Alexander N.

doi:10.1016/j.jfluchem.2009.09.013

Cited by 3 publications

(2 citation statements)

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“…β‐Enamino esters are versatile intermediates, which are often used for the synthesis of heterocycles, and compounds of this class are also common pharmacophores in a number of important medicinal agents 1. Furthermore, β‐enamino esters are employed as key starting reagents for the synthesis of substituted pyrazoles,2 substituted aromatic amines,3 substituted pyrroles,4 1,4‐dihydropyridine derivatives,5 functionalized pyrimidines,6 benzo[ g ]isoquinolines,7 2‐azaspiro[4,5]decatrienes,8 1,2,3‐triazole derivatives,9 indolequinones,10 2‐substituted‐1,4‐quinones,11 C ‐glycosides,12 2‐pyrrolidone derivatives,13 2‐oxo‐[1,4]oxazino[3,2‐ e ]indoles,14 4‐thioxopyrimidines,15 and 5‐hydroxyindole derivatives 16…”

Section: Initial Evaluation Of the Reaction Conditions[a]mentioning

confidence: 99%

“…[1] Furthermore, b-enamino esters are employed as key starting reagents for the synthesis of substituted pyrazoles, [2] substituted aromatic amines, [3] substituted pyrroles, [4] 1,4-dihydropyridine derivatives, [5] functionalized pyrimidines, [6] benzo [g]isoquinolines, [7] 2-azaspiroA C H T U N G T R E N N U N G [4,5]decatrienes, [8] 1,2,3-triazole derivatives, [9] indolequinones, [10] 2-substituted-1,4-quinones, [11] Cglycosides, [12] 2-pyrrolidone derivatives, [13] 2-oxo- [1,4] [14] 4-thioxopyrimidines, [15] and 5-hydroxyindole derivatives. [1] Furthermore, b-enamino esters are employed as key starting reagents for the synthesis of substituted pyrazoles, [2] substituted aromatic amines, [3] substituted pyrroles, [4] 1,4-dihydropyridine derivatives, [5] functionalized pyrimidines, [6] benzo [g]isoquinolines, [7] 2-azaspiroA C H T U N G T R E N N U N G [4,5]decatrienes, [8] 1,2,3-triazole derivatives, [9] indolequinones, [10] 2-substituted-1,4-quinones, [11] Cglycosides, [12] 2-pyrrolidone derivatives, [13] 2-oxo- [1,4] [14] 4-thioxopyrimidines, [15] and 5-hydroxyindole derivatives.…”

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confidence: 99%

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The Construction of Polysubstituted Aromatic Core Derivatives via a Cycloaddition/Oxidative Aromatization Sequence from Quinone and β‐Enamino Esters

Huang

et al. 2014

Adv Synth Catal

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An unexpected strategy has been discovered for the construction of polysubstituted aromatic core derivatives from the reaction of quinones or N-substituted maleimides with b-enamino esters by a cycloaddition/oxidative aromatization sequence that provides products contrary to those delivered by the Nenitzescu reaction. The current method provides a highly favorable synthetic strategy for the efficient construction of important therapeutic agents containing polysubstituted aromatic core structures.b-Enamino esters are versatile intermediates, which are often used for the synthesis of heterocycles, and compounds of this class are also common pharmacophores in a number of important medicinal agents. [1] Furthermore, b-enamino esters are employed as key starting reagents for the synthesis of substituted pyra-Quinones represent one of the most widely distributed structural classes in nature, [17] and compounds belonging to this class can be found in a large number of important pharmacophores [18] associated with anti-cancer, antibacterial, antimalarial, fungicidal, and antiparasitic agents. [19] Based on the recent resurgence of interest in the functionalization of quinone structures [20] and the application of b-enamino esters in organic synthesis, [21] we became interested in further exploring the reactions of b-enamino esters with quinones.During the course of our research in this area, an unexpected product, diethyl 9,10-anthraquinone-1,3dicarboxylate (3a), was discovered involving the reaction of 1,4-naphthoquinone (1a) with ethyl-3-(methylamino)acrylate (2a) [Eq. (2)]. Contrary to similar work reported by MenØndez et al. [Eq.(1)], [22] however, where the Nenitzescu reaction was used to obtain fused indoles, our own work led to the formation of a different product 3a, with the difference in the products being attributed to the presence of an H atom instead of a methyl group at the R 2 position of the b-enamino esters under the same conditions as reported by MenØndez (Table 1, entry 1).Furthermore, among various kinds of naturally occurring substances, quinone derivatives are common and very important. [23] For example, rhein, [24] physcion, [23d,25] aloe-emodin; [26] emodin [27] and chrysophanol [28] exhibit antifungal activity. [23d,29] Especially emodin, which is purified from the Chinese medicinal herb rhubarb, has inhibitory activity against ERK phosphorylation in PC3 cells induced by EGF. [30] Moreover, aloe-emodin might represent a conceptually new lead antitumor drug taking into account its unique cytotoxicity profile and mode of action. [26a] Besides, DMAC, aloesaponarin I and aloesaponarin II also show good antibacterial activity (Figure 1). [31] Based on this initial result and the significance of these unexpected polysubstituted aromatic cores in related drugs, we became interested in developing a greater understanding of this reaction between 1,4-

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