Reactions of 1-bromo-1-nitro-3,3,3-trichloropropene with acetylacetone and cyclohexane-1,3-dione

Makarenko, S. V.; Stukan, E. V.; Trukhin, E. V.; Berestovitskaya, V. M.

doi:10.1134/s1070363215100126

Cited by 2 publications

(1 citation statement)

References 9 publications

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“…Conjugated nitroalkenes are versatile reagents in organic synthesis . Their reactions with nucleophiles allow to obtaining various heterocycles, functional derivatives, and many other compounds including biologically active ones. − Nitroalkenes are used as alkylating agents in reactions with arenes and heteroarenes promoted by Brønsted superacids , or Lewis acids …”

Section: Introductionmentioning

confidence: 99%

Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF₃SO₃H: Synthesis of (Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism

et al. 2018

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3,3,3-Trihalogeno-1-nitropropenes C(Hal)CH═CH(NO) (Hal = F, Cl, Br) in reaction with arenes in the superacid CFSOH (TfOH) at room temperature in 1 h afford 3,3,3-trihalogeno-1,2-diarylpropan-1-one oximes C(Hal)CH(Ar)-C(Ar)═NOH (CHal-oximes) in yields of 23-99%. Such CHal-oximes having one ortho-substituent in the aryl ring exist as atropoisomers in solutions at room temperature. Several cationic intermediates of this reaction were studied by means of NMR and DFT calculations, which proves the detailed reaction mechanism of the formation of CHal-oximes in TfOH. CHal-oximes (for Hal = Cl, Br) with DBU in DMF at microwave or thermal activation are cyclized into 5-halogeno-3,4-diarylisoxazoles in yields of 37-59%. CHal-oximes under the conditions of Beckmann rearrangement with PCl in benzene at room temperature in 24 h are turned at first into imidoyl chlorides (yields of 94-96%), which undergo transformation into the corresponding benzamides PhCONHCHPh(CHal) on silica gel (yields of 46-47%).

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Section: Introductionmentioning

confidence: 99%

Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF₃SO₃H: Synthesis of (Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism

et al. 2018

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Ethyl 3-halo-3-nitroacrylates: synthesis and reactions with primary aromatic amines

et al. 2021

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Reactions of 1-bromo-1-nitro-3,3,3-trichloropropene with acetylacetone and cyclohexane-1,3-dione

Cited by 2 publications

References 9 publications

Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF₃SO₃H: Synthesis of (Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism

Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF₃SO₃H: Synthesis of (Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism

Ethyl 3-halo-3-nitroacrylates: synthesis and reactions with primary aromatic amines

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Reactions of 1-bromo-1-nitro-3,3,3-trichloropropene with acetylacetone and cyclohexane-1,3-dione

Cited by 2 publications

References 9 publications

Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF3SO3H: Synthesis of (Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism

Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF3SO3H: Synthesis of (Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism

Ethyl 3-halo-3-nitroacrylates: synthesis and reactions with primary aromatic amines

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Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF₃SO₃H: Synthesis of (Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism

Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF₃SO₃H: Synthesis of (Z)-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism