Synthesis and Herbicidal Activity of 3-Hexyl-4-R-6,7-dimethoxy Isocoumarin

Huo, Jingqian; Zhang, Zhe; Dong, Hanqing; Zhang, Jinlin; Shi, Jiamei

doi:10.14233/ajchem.2016.19473

Cited by 3 publications

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“…Isocoumarins are an important building block in synthetic medicinal chemistry because they have shown interesting bioactivities, for example, as anticoagulants (Oweida et al, 1990), as herbicides (Zhang et al, 2016) and as insecticides (Qadeer et al, 2007). In order to gain access to compounds of this type in a straightforward way, a synthetic route has been developed using reactions between 2-formylbenzoic acid, hydrogen cyanide and anilines to yield N-aryldiaminoisocoumarins (Opatz & Ferenc, 2005).…”

Section: Introductionmentioning

confidence: 99%

Conversion of 3-amino-4-arylamino-1H-isochromen-1-ones to 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones: synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative

et al. 2020

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An efficient synthesis of 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones, involving the diazotization of 3-amino-4-arylamino-1H-isochromen-1-ones in weakly acidic solution, has been developed and the spectroscopic characterization and crystal structures of four examples are reported. The molecules of 1-phenylisochromeno[3,4-d][1,2,3]triazol-5(1H)-one, C 15 H 9 N 3 O 2 , (I), are linked into sheets by a combination of C-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds, while the structures of 1-, each contain just one hydrogen bond which links the molecules into simple chains, which are further linked into sheets by -stacking interactions in (II) but not in (III). In the structure of 1-(4chlorophenyl)isochromeno [3,4-d][1,2,3]triazol-5(1H)-one, (IV), isomeric with (III), a combination of C-HÁ Á ÁO and C-HÁ Á Á(arene) hydrogen bonds links the molecules into sheets. When compound (II) was exposed to a strong acid in methanol, quantitative conversion occurred to give the ring-opened transesterification product methyl 2-[4-hydroxy-1-(2-methylphenyl)-1H-1,2,3-triazol-5-yl]benzoate, C 17 H 15 N 3 O 3 , (V), where the molecules are linked by paired O-HÁ Á ÁO hydrogen bonds to form centrosymmetric dimers.

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Section: Introductionmentioning

confidence: 99%

Conversion of 3-amino-4-arylamino-1H-isochromen-1-ones to 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones: synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative

et al. 2020

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“…I as antimicrobial [77], anti-inflammatory [78], and antitumor [79][80] agents and in inhibition of hepatitis C virus [81][82][83], however, their natural abundance in plants is very low and the purification processes are complex. Therefore, various methods have been developed for the total synthesis of coumarins [84][85][86], including the Perkin [87], Pechmann [88], and Knoevenagel reactions [89].…”

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confidence: 99%

Synthesis of Bioactives Coumarin Derivatives, Phthalocyanines and Terminal Conjugated Dienes via a Ruthenium Catalyzed Cross-Metathesis: Application to Renewable Resources

Bilel

Medyouni

Al‐Ayed

et al. 2016

MSF

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This study aimed for the synthesis of 4-Aryl-2-amino-6-(4-hydroxy coumarin-3-yl) pyridine-3-carbonitriles derivatives 4, suitable for use as antibacterial, anti-oxidant and anti-inflammatory activities via a versatile, readily accessible 3-((2E)-3(aryl)prop-2-enoyl)-2H-chromen-2-one, 3, which was prepared by refluxing 3-acetyl-4-hydroxycoumarin with aromatic aldehydes in chloroform in the presence of a catalytic amount of piperidine. Then the direct reaction of the obtained chalcones 3 with malonitrile in the presence of ammonium acetate in one step gave products 4. Most of the new compound 4 exhibit moderate antibacterial activity against Gram Negative bacterial strains (E. coli, K. pneumonia, S. typhi and S. flexneri). In addition, the compounds 4 were investigated for anti-oxidant activities by super oxide radical, DPPH (2,2-Diphenyl-1-picrylhydrazyl), and hydroxyl radical scavenging assays, where most of the compounds displayed significant antioxidant activities. Furthermore, these 4-Aryl-2-amino-6-(4-hydroxy coumarin-3-yl) pyridine-3-carbonitriles 4 were evaluated for anti-inflammatory activity by indirect haemolytic and lipoxygenase inhibition assays where compounds revealed good activity. The preparation of novel metal-free phthalocyanines and metallophthalocyanine complexes 11 and 12 (MPcs, M = Co, Zn, Cu and Mn), with four peripheral 6-hydroxy-4-methylcoumarin and 6-hydroxycoumarin substituents, were also prepared by cyclotetramerization of compounds 7 and 10 with the corresponding metal salts (Zn(OAc)2.2H2O, Co(OAc)2.4H2O, CuCl, Mn(OAc)2.4H2O) as a template for macrocycle formation in 2-(N,N-dimethylamino)ethanol.The electronic spectra of these compounds exhibit a band of coumarin identity together with characteristic bands of the phthalocyanine core. The new compounds were screened for antibacterial activity. Most of them are active against E. coli and S. aureus. In addition, some novel 3-acetylcoumarin derivatives 17 were prepared in good yields. Their invitro antioxidant activities were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity method. In this way, novel coumarin phtalonitriles derivatives 42-44 were synthesized.The synthesis of these coumarin phtalonitriles was resulting from a nucleophilic aromatic substitution reaction between 4-nitrophtalonitrile and coumarins derivatives. The complexing properties of the coumarin derivatives toward alkali metal, alkaline earth metal, some transition metals and some heavy metal cations have been investigated in acetonitrile by means of UV spectrophotometry absorption and conductivity methods. Thus, the stoichiometry of the complexes formed and their stability constants were determined. We report also in this book chapter a sequence of two ruthenium-catalyzed transformations, namely olefin cross metathesis with allylic chloride followed by elimination, which gives a straightforward access to terminal 1,3-dienes from natural products. The structures of all the new obtained compounds were confirmed by elemental analysis, IR, and multinuclear/multidimensional NMR spectroscopy (1H, 13C-NMR, NOESY, HMBC) which allowed assignment of the complete network of proton and carbon atoms).

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Divergent syntheses of iodinated isobenzofuranones and isochromenones by iodolactonization of 2-alkynylbenzoic acids in ionic liquids

et al. 2017

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The regiochemical outcome of the iodolactonization of 2-alkynylbenzoic acids, carried out at 100 °C in ionic liquids (ILs) as unconventional solvents and with molecular iodine as the iodine source, in the absence of external bases, was found to be strongly dependent on the nature of the IL medium. In particular, while the use of N-ethyl-N-methylmorpholinium dicyanamide (MorN(CN)) promoted the stereoselective formation of (E)-3-(iodomethylene)isobenzofuran-1(3H)-ones, through an anti-5-exo-dig cyclization route, the use of 1-ethyl-3-methylimidazolium ethyl sulfate (EmimEtSO) tended to favor the 6-endo-dig cyclization mode, with preferential or selective formation of 4-iodo-1H-isochromen-1-ones. In any case, the IL solvent could be easily recycled after extraction of the product from the reaction mixture with diethyl ether. DFT calculations have been carried out to clarify the role of the IL's nature in favoring either the anti-5-exo-dig cyclization route or the 6-endo-dig mode. In the case of iodocyclization of 2-ethynylbenzoic acid, only the 5-exo-dig mode was observed in both EmimEtSO and MorN(CN) solvents. The structures of two representative products have been confirmed by X-ray diffraction analysis.

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Synthesis and Herbicidal Activity of 3-Hexyl-4-R-6,7-dimethoxy Isocoumarin

Cited by 3 publications

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Conversion of 3-amino-4-arylamino-1H-isochromen-1-ones to 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones: synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative

Conversion of 3-amino-4-arylamino-1H-isochromen-1-ones to 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones: synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative

Synthesis of Bioactives Coumarin Derivatives, Phthalocyanines and Terminal Conjugated Dienes via a Ruthenium Catalyzed Cross-Metathesis: Application to Renewable Resources

Divergent syntheses of iodinated isobenzofuranones and isochromenones by iodolactonization of 2-alkynylbenzoic acids in ionic liquids

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