Formylation and dichloromethylation as alternative directions of rieche reaction. A novel to the synthesis of sterically hindered aromatic dialdhydes

Yakubov, A. P.; Tsyganov, Dmitry V.; Беленький, Л. И.; Krayushkin, M. M.

doi:10.1016/s0040-4020(01)90166-8

Cited by 14 publications

(10 citation statements)

References 14 publications

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“…The synthesis of 3,5‐bis(azidomethyl)‐2,4,6‐trimethylbenzaldehyde ( 4 ) was based on the synthesis of mesitaldehyde by treatment of aromatic compounds with dichloromethyl methyl ether in the presence of a Lewis acid such as TiCl 4 18. However, reaction of the known 1,3‐bis(bromomethyl)‐2,4,6‐trimethylbenzene ( 1 )19 and dichloromethyl methyl ether resulted in the formation of not only 3,5‐bis(bromomethyl)‐2,4,6‐trimethylbenzaldehyde ( 2 ) but also 3‐bromomethyl‐5‐chloromethyl‐2,4,6‐trimethylbenzaldehyde ( 3 ), according to mass and 1 H NMR spectroscopy analyses.…”

Section: Resultsmentioning

confidence: 99%

Click Reaction Synthesis and Photophysical Studies of Dendritic Metalloporphyrins

et al. 2014

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Several dendritic zinc(II)‐porphyrins bearing carbazole units at the terminals have been prepared through click reaction of azide‐substituted Zn‐porphyrin precursors and carbazole‐based alkynes under [Cu(NCCH3)4][PF6] catalysis. This family of new dendritic metalloporphyrins shows dual luminescence from both the upper S2 and the lowest S1 singlet states. The observed trends in the spectroscopic data and the photophysical properties of the dendrimers have been rationalized in terms of the type of meso‐spacer between the macrocycle and dendritic shell. The key feature of the meso‐spacer is proposed to be the degree of hindrance towards aryl ring rotation relative to the mean porphyrin plane. Based on the observed differences in the S1→S0 fluorescence quantum yield on going from four‐ to five‐coordinate dendrimers, it was shown that dendrimer architectures with all four meso‐aryl spacers sterically hindered, are most appropriate to monitor processes related to axial ligation of the dendrimer core, since they provide larger luminescence response differences between the four‐coordinate and five‐coordinate forms. The blue S2→S0 fluorescence quantum yield has been measured and the observed trend has been rationalized in terms of the S2→S1 energy gap law. No significant differences were observed between the compounds either with different rotational degree of freedom of the meso‐spacers or with different ligation states of the dendrimer core.

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Section: Resultsmentioning

confidence: 99%

Click Reaction Synthesis and Photophysical Studies of Dendritic Metalloporphyrins

et al. 2014

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“…2,4,5,6-Tetraehloroisophthlalic aldoxime (7). A solution of hydroxylamine hydrochloride (2.92 g, 0.042 tool) and sodium acetate (3.44 g, 0.042 tool) in 15 mL of water was added to a boiling solution of aldehyde 3 (3.9 g, 0.014 tool) in 50 mL of EtOH.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of tetrachloroisophthalic and-terephthalic aldehydes and stable bis(nitrile oxides) based on them

et al. 1997

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A new route for the synthesis of 2,4.5,6-tetrachloroisophtha)ic and 2.3.5.6-tetrachloroterephthalic aldehydes from the corresponding tetrachlorobenzenes was developed. The method involves dichloromethylation of the initial compounds with chloroform in the presence of aluminum chloride and subsequent hydrolysis of the resulting 1.3-bis(dichloromethyl)-2,4,5,6-tetrachlorobenzene and 1,4-bis(dichloromethyl)-2,3,5.6-tetrachlorobenzene. Stable 2,4.5,6-tetrachlorobenzene-l,3-dicarbonitrile oxide and 2,3.5.6-tetrachlorobenzene-1,4-dicarbonitrile oxide were obtained for the fir'st time from the above aldehydes via the corresponding oximes. The products w-re characterized by IR and t3C NMR spectra, and were converted into substituted 1,3-and 1,4-phenylenebis(isoxazolines) using 1.3-dipolar cycloaddition with styrene.

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“…Compound 21 was obtained by replacing acrylic acid with methacrylic acid in the Heck reaction and ester 22 was obtained by treating the acyl fluoride 10 with isopropanol instead of isopropylamine. The vinylogue 23 was obtained by a Rieche formylation of commercial p-methoxybenzoic acid followed by the deoxofluorination/condensation protocol used for the synthesis of 11b [39,40]. Naphthalene derivatives 24 and 25 were obtained in a similar way as 23.…”

Section: Structure Activity Relationship Studies (Sar) On Compound 11bmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Difluoromethyl Cinnamoyl Amides

et al. 2020

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Series of novel amides of isoferulic acid, where the phenolic hydroxyl was replaced by a difluoromethyl group, were synthesized and their in vitro antibacterial activities assayed against fourteen bacterial strains (six Gram-positive and eight Gram-negative). A one-pot methodology was developed to obtain the 3′-(difluoromethyl)-4′-methoxycinnamoyl amides using Deoxofluor® as a fluorinating agent. The N-isopropyl, N-isopentyl, and N-(2-phenylethyl) amides 11b, 11d and 11g were the most active and selective against Mycobacterium smegmatis (MIC = 8 µg/mL) with 11b and 11g displaying negligible or no cytotoxicity against HepG2 and A549 cells. Thirteen analogs of N-isopropylamide 11b were also synthesized and their antibacterial activity assayed. Results show that the difluoromethyl moiety enhanced antibacterial activity and selectivity towards M. smegmatis, changing the microorganism inhibition profile of the parent compound. The selectivity exhibited by some of the compounds towards M. smegmatis makes them potential leads in the search for new narrow spectrum antibiotics against M. tuberculosis.

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Formylation and dichloromethylation as alternative directions of rieche reaction. A novel to the synthesis of sterically hindered aromatic dialdhydes

Cited by 14 publications

References 14 publications

Click Reaction Synthesis and Photophysical Studies of Dendritic Metalloporphyrins

Click Reaction Synthesis and Photophysical Studies of Dendritic Metalloporphyrins

Synthesis of tetrachloroisophthalic and-terephthalic aldehydes and stable bis(nitrile oxides) based on them

Synthesis and Antibacterial Activity of Difluoromethyl Cinnamoyl Amides

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