Trifluoromethyl-containing N-acylmethylenequinone imines as novel highly electrophilic agents

Dyachenko, V. I.; Peregudov, A. S.; Чкаников, Н. Д.

doi:10.1016/j.jfluchem.2007.04.008

Cited by 3 publications

(1 citation statement)

References 18 publications

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“…Among them, the most important and efficient approaches involve the use of electrophilic isatins/isatinimines and nucleophilic 3-monosubstituted oxindoles for the synthesis of 3,3′-disubstituted oxindoles ( Figure 1 ) [ 2 , 3 , 4 , 5 , 12 , 13 ]. Despite these advances, however, the use of indol-2-ones (generated in situ from 3-halooxindoles) as electrophiles has been limited [ 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

Alcohols as Substrates and Solvents for the Construction of 3-Alkoxylated-2-Oxindoles by Direct Alkoxylation of 3-Halooxindoles

et al. 2017

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Described herein is an environmentally benign method for the synthesis of multisubstituted 3-alkoxylated-2-oxindoles 3 via direct alkoxylation of 3-halooxindoles 1. A wide variety of such multisubstituted 3-alkoxylated-2-oxindole scaffolds were smoothly obtained in good yields (up to 94%) by heating in an oil bath at 35 °C for 24 h. A particularly valuable feature of this method was the development of environment-friendly chemistry using alcohols 2 as both the substrates and solvents in the presence of a catalytic amount of base.

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Section: Introductionmentioning

confidence: 99%

Alcohols as Substrates and Solvents for the Construction of 3-Alkoxylated-2-Oxindoles by Direct Alkoxylation of 3-Halooxindoles

et al. 2017

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Trifluoromethyl‐Containing N‐Acylmethylenequinone Imines as Novel Highly Electrophilic Agents.

2007

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Quinone derivatives Q 0410Trifluoromethyl-Containing N-Acylmethylenequinone Imines as Novel Highly Electrophilic Agents. -A convenient method for the synthesis of highly electrophilic CF3-containing N-acyl-p-methylenequinone imines is developed and exemplified by the synthesis of compound (V). Reactions of p-methylenequinone imines as well as metastable N-acyl-o-methylenequinone imines derived from 3-chloro-3-trifluorodihydroindolones (XV) with N-, O-, and C-nucleophiles are studied. -(DYACHENKO*, V. I.; PEREGUDOV, A. S.; CHKANIKOV, N. D.; J. Fluorine Chem. 128 (2007) 7, 868-878; Nesmeyanov Inst. Organoelem. Compd., Russ. Acad. Sci., Moscow 119991, Russia; Eng.) -H. Toeppel 45-074

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Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation

Zhang

Zhuang

et al. 2013

Org. Biomol. Chem.

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Diverse reactivity by coupling of substituted anilines with ethyl trifluoropyruvate was developed under microwave irradiation without catalysts to generate 3-trifluoromethyl-3-hydroxy oxindoles, aromatic hydroxy trifluoromethyl esters, and 1,2-dicarbonyl compounds in a fast and efficient manner. The plausible mechanism for obtaining different products was proposed. Furthermore, the anti-HIV activity of aromatic hydroxy trifluoromethyl esters was first reported. The best inhibitory activity against wild-type HIV-1 IIIB was exemplified by trifluoromethyloxindole 3q with an IC50 = 5.8 μM, which also displayed potential activity against Y181C mutant virus with an IC50 = 7.5 μM. More significantly, the activities of oxindoles 3q and 3r to inhibit K103N/Y181C double mutant HIV-1 reverse transcriptase (RT) are probably similar to that of the second-generation nonnucleoside inhibitor HBY 097 by docking calculation.

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Trifluoromethyl-containing N-acylmethylenequinone imines as novel highly electrophilic agents

Cited by 3 publications

References 18 publications

Alcohols as Substrates and Solvents for the Construction of 3-Alkoxylated-2-Oxindoles by Direct Alkoxylation of 3-Halooxindoles

Alcohols as Substrates and Solvents for the Construction of 3-Alkoxylated-2-Oxindoles by Direct Alkoxylation of 3-Halooxindoles

Trifluoromethyl‐Containing N‐Acylmethylenequinone Imines as Novel Highly Electrophilic Agents.

Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation

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