Synthesis of 2‐Cyanoacrylates Containing Pyridinyl Moiety under Ultrasound Irradiation.

Zhang, Huiping; Song, Baoan; Zhong, Huimin; Yang, Song; Jin, Linhong; Hu, Deyu; He, Wei

doi:10.1002/chin.200604131

Cited by 1 publication

(3 citation statements)

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“…The typical phosphorus resonance at 18.78-20.80 ppm in the 31 P NMR spectra of all target compounds confirmed the presence of a phosphorus center coupled to adjacent CH. All of the nonequivalent carbon atoms were identified in 13 C NMR and the total number of protons calculated from the integration curve accorded (in 1 H NMR) with the assigned structures.…”

Section: Resultsmentioning

confidence: 69%

“…Because the reaction rates for the synthesis of cyanoacrylates and R-aminophosphonates are found to be markedly accelerated under microwave irradiation (14,21), we undertook the synthesis of the title compounds under similar conditions for improving reaction yields and shortening reaction times (Scheme 1). Compounds II were completely characterized by IR, 1 H, 13 C, 31 P NMR, and elemental analysis data. Some of the synthesized compounds showed excellent anti-TMV activities.…”

Section: Introductionmentioning

confidence: 99%

“…2-Cyanoacrylates and their derivatives act as potent growth inhibitors of weeds due to their ability to disrupt photosystem II (PSII) electron transport at a common binding domain on the 32 kDa polypeptide at the PSII reaction center − . These compounds exhibit a wide range of bioactivities with immense potential to be employed as herbicides, fungicides, plant virucides, and antitumor agents − . Some of these cyanoacrylate derivatives obtained by conventional nucleophilic displacement of methylthio moieties of 2-cyano-3-(methylthio) acrylates by ( R )- or ( S )-1-phenylethanamine, phenylamino group, and aryl (heterocyclic) amine displayed moderate to good effect against tobacco mosaic virus (TMV) in vivo , .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antiviral Bioactivities of 2-Cyano-3-substituted-amino(phenyl) Methylphosphonylacrylates (Acrylamides) Containing Alkoxyethyl Moieties

Yang

Song

Bhadury

et al. 2009

J. Agric. Food Chem.

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An efficient reaction under microwave irradiation has been developed for the synthesis of a series of novel 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) II. The products obtained in shorter reaction time with moderate yields are fully characterized by elemental analysis, IR, (1)H, (13)C, and (31)P NMR spectral data. The role of introducing various substituents and the effect of incorporating alpha-aminophosphonates with an alkoxyethyl moiety into the parent cyanoacrylate (acrylamide) structure are investigated. Among the studied compounds, both II-17 and II-24 displayed good in vivo curative, protection, and inactivation effects, which were comparable to those of the commercial reference ningnanmycin (inhibitory rates of 58.8, 60.2, 78.9% and 60.0, 58.9, 85.5%, respectively, at 500 mg/L against TMV). To the best of the authors' knowledge, this is the first report on the synthesis and antiviral activity of the title compounds II.

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Section: Resultsmentioning

confidence: 69%