Studies on fluorine-containing heterocyclic compounds. 3. Reactions of 3,5-dinitro-2-chlorobenzotrifluoride and 3,5-dinitro-4-chlorobenzotrifluoride with sulfur and nitrogen-containing nucleophiles

Chi, Ching-Sung; Chen, Mei-Jen; Liang, Shi-Quin; Chen, Dehua

doi:10.1016/s0022-1139(00)81068-4

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Jul-aug 20011

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Cited by 5 publications

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“…They react with (1,2 nn) species, like ethyl thioglycolate, benzylmercaptan [119], amino acid esters [120,121], hydrazines, and hydroxylamines [122], to yield trifluoromethyl-substituted naphthothiophenes, benzindoles, benzindazoles, and naphthoisoxazoles, respectively (Scheme 20).…”

Section: Jul-aug 2001mentioning

confidence: 99%

Recent trends in the Chemistry of fluorinated five and six‐membered heterocycles

Erian

2001

Journal of Heterocyclic Chem

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Section: Jul-aug 2001mentioning

confidence: 99%

Recent trends in the Chemistry of fluorinated five and six‐membered heterocycles

Erian

2001

Journal of Heterocyclic Chem

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ChemInform Abstract: Studies on Fluorine‐Containing Heterocyclic Compounds. Part 3. Reactions of 3,5‐Dinitro‐2‐chlorobenzotrifluoride and 3,5‐Dinitro‐4‐chlorobenzotrifluoride with Sulfur‐ and Nitrogen‐Containing Nucleophiles.

Chi¹,

Chen²,

Liang³

et al. 1988

ChemInform

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ChemInform Abstract The chlorodinitrobenzotrifluorides (I) and (IV) mentioned in the title react with methyl thioglycolate (II) and triethylamine at room temperature, forming the benzothiazole N-oxides (III) or (V). (V) is converted to the nitroso derivatives (VI) upon refluxing with further (II). (IV) is coupled with the α-amino esters (VII) at room temperature, yielding the phenylamino esters (VIII). Reactions of (IV) with (VIIa) in refluxing ethanol, however, yields the ring closure products (IX) and (X).

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1,3‐Dinitro‐2‐chloro‐5‐trifluorotoluene and its bridged derivatives I. An investigation on the displacement reactions of bidentate nucleophiles towards aromatic rings

Ji¹,

Chen²,

Wang³

et al. 1991

Chin. J. Chem.

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The reactions of 1,3‐dinitro‐2‐chloro‐5‐trifluorotoluene (DNCTT) (1) and its bridged compounds with bidentate nucleophiles have been investigated. Primary or secondary diamines and diethylene glycol react with 1 and its bridged derivatives by replacing the substituent group para to CF3, whereas ethanedithiol reacts either by replacing the substituent group para to CF3 or by displacing both groups and a nitro group. The results have been rationalized in terms of electronic effects and nucleophilicity of the nucleophiles.

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Studies on fluorine-containing heterocyclic compounds. 3. Reactions of 3,5-dinitro-2-chlorobenzotrifluoride and 3,5-dinitro-4-chlorobenzotrifluoride with sulfur and nitrogen-containing nucleophiles

Cited by 5 publications

References 3 publications

Recent trends in the Chemistry of fluorinated five and six‐membered heterocycles

Recent trends in the Chemistry of fluorinated five and six‐membered heterocycles

ChemInform Abstract: Studies on Fluorine‐Containing Heterocyclic Compounds. Part 3. Reactions of 3,5‐Dinitro‐2‐chlorobenzotrifluoride and 3,5‐Dinitro‐4‐chlorobenzotrifluoride with Sulfur‐ and Nitrogen‐Containing Nucleophiles.

1,3‐Dinitro‐2‐chloro‐5‐trifluorotoluene and its bridged derivatives I. An investigation on the displacement reactions of bidentate nucleophiles towards aromatic rings

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