Chemistry of Polyhalogenated Nitrobutadienes, 12: Synthesis of Novel, Highly Substituted Bi- and Tricyclic 5,6,7,8-Tetrahydro-4H-chromen-5-ones

Kaufmann, Dieter; Zapol’skii, V. A.; Vogt, Eva-Janina; Gjikaj, Mimoza

doi:10.3987/com-12-s(n)108

Cited by 7 publications

(2 citation statements)

References 35 publications

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“…The next successive steps were performed with the most stable derivative 3-morpholino-4-nitro-5-(vinylthio)thiophene-2-carbaldehyde (55) [82]. Knoevenagel condensation of thiophene 55 with malononitrile in ethanol in the presence of a catalytic amount of sodium ethanolate gave the gem-dicyanovinylthiophene 56 in 68% yield [83]. Oxidation of the vinylsulfanylthiophene 56 with threefold excess of hydrogen peroxide in acetic acid at 50-55 • C furnished sulfone 57 in 82% yield.…”

Section: Thiophenesmentioning

confidence: 99%

Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

Zapol’skii

Bilitewski²,

Kupiec³

et al. 2020

Molecules

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Substituted nitrogen heterocycles are structural key units in many important pharmaceuticals. A new synthetic approach towards heterocyclic compounds displaying antibacterial activity against Staphylococcus aureus or cytotoxic activity has been developed. The selective synthesis of a series of 64 new N-heterocycles from the three nitrobutadienes 2-nitroperchloro-1,3-butadiene, 4-bromotetrachloro-2-nitro-1,3-butadiene and (Z)-1,1,4-trichloro-2,4-dinitrobuta-1,3-diene proved feasible. Their reactions with N-, O- and S-nucleophiles provide rapid access to push-pull substituted benzoxazolines, benzimidazolines, imidazolidines, thiazolidinones, pyrazoles, pyrimidines, pyridopyrimidines, benzoquinolines, isothiazoles, dihydroisoxazoles, and thiophenes with unique substitution patterns. Antibacterial activities of 64 synthesized compounds were examined. Additionally, seven compounds (thiazolidinone, nitropyrimidine, indole, pyridopyrimidine, and thiophene derivatives) exhibited a significant cytotoxicity with IC50-values from 1.05 to 20.1 µM. In conclusion, it was demonstrated that polyhalonitrobutadienes have an interesting potential as structural backbones for a variety of highly functionalized, pharmaceutically active heterocycles.

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Section: Thiophenesmentioning

confidence: 99%

Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

Zapol’skii

Bilitewski²,

Kupiec³

et al. 2020

Molecules

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“…The corresponding syntheses that we have developed up to now [2–13], always start with the attack of an appropriate nucleophile at the activated terminal carbon atom of the nitrodichlorovinyl group within 1 to undergo a vinylic substitution. Thus, in case of, e.g., sulfur nucleophiles, the corresponding thioperchlorobutadiene derivatives are easily accessible [2,5,16–17].…”

Section: Introductionmentioning

confidence: 99%

Chemistry of polyhalogenated nitrobutadienes, 14: Efficient synthesis of functionalized (Z)-2-allylidenethiazolidin-4-ones

Zapol’skii¹,

Namyslo²,

Gjikaj³

et al. 2014

Beilstein J. Org. Chem.

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SummaryThe reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene (1) provides an appropriate precursor for the synthesis of special thiazolidin-4-ones. Applying different anilines as the second constituent for the requisite cyclization step, a series of (Z)-2-allylidenethiazolidin-4-ones was obtained in yields up to 81%. Some subsequent reactions have been examined too, such as the formation of perfunctionalized 1H-pyrazoles upon treatment with hydrazine. Thiazolidinones are as well known for their physiological activities as for their application in optoelectronics.

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ChemInform Abstract: Chemistry of Polyhalogenated Nitrobutadienes. Part 12. Synthesis of Novel, Highly Substituted Bi‐ and Tricyclic 5,6,7,8‐Tetrahydro‐4H‐chromen‐5‐ones.

et al. 2013

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-Knoevenagel condensation of 3,4-push-pull-substituted thiophene-2-carbaldehydes 4 with malononitrile gives the gem-dicyanovinylthiophenes 5, followed by a Michael addition of dimedone and a subsequent cyclization to 4-(2-thienyl)-5,6,7,8-tetrahydro-4H-chromen-5-ones 6. Protonolysis of the latter in methanol led to a mixture of four heterocycles 7-10, the main product being the novel tricyclic 9-(2-thienyl)-6,7-dihydro-5H-thieno[3,2-b]chromen-8(9H)-one derivative 7. A mechanism of the protonolysis reaction is proposed, the structures of the two products 7a/8a have been confirmed by X-ray analysis.

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Chemistry of Polyhalogenated Nitrobutadienes, 12: Synthesis of Novel, Highly Substituted Bi- and Tricyclic 5,6,7,8-Tetrahydro-4H-chromen-5-ones

Cited by 7 publications

References 35 publications

Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

Polyhalonitrobutadienes as Versatile Building Blocks for the Biotargeted Synthesis of Substituted N-Heterocyclic Compounds

Chemistry of polyhalogenated nitrobutadienes, 14: Efficient synthesis of functionalized (Z)-2-allylidenethiazolidin-4-ones

ChemInform Abstract: Chemistry of Polyhalogenated Nitrobutadienes. Part 12. Synthesis of Novel, Highly Substituted Bi‐ and Tricyclic 5,6,7,8‐Tetrahydro‐4H‐chromen‐5‐ones.

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