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2 protocols using substitutedaryl aldehyde

1

Synthesis of Arylmethylidene Azlactones

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All the starting materials, substituted
aryl aldehyde, 4-toluenesulfonylmethyl isocyanide (TosMIC), triethylamine,
diisopropylethylamine, N-methylmorpholine, imidazole,
sodium bicarbonate, potassium carbonate, potassium phosphate tribasic
(anhydrous, reagent grade > 98%), and 2-propanol (anhydrous, 99.5%),
were purchased from Sigma-Aldrich, and solvents were used from commercial
suppliers without further purification. Analyses of 1H
NMR and 13C NMR were performed by a Bruker DRX400 spectrometer
(400 MHz). Chemical shifts are reported in parts per million (ppm)
relative to the internal standard. Coupling constants (J) are given in hertz (Hz). Multiplicities of peaks are given as d
(doublet), m (multiplet), s (singlet), and t (triplet). The removal
of the solvent was carried out by a rotary evaporator under reduced
pressure. IR spectra were recorded on a Bomen DA8 3 FTS spectrometer.
GC–MS has been recorded using a Perkin Elmer Clarus 600C spectrometer.
Microwave-assisted reactions were carried out in a catalyst scientific
microwave oven system (model no: CATA R; Catalyst System, Pune) operating
at 2450 MHz equipped with glass vial extension by a condenser used
for performing the reaction. The microwave was equipped with a temperature
control system (external probe).
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2

Spectroscopic Characterization of Organic Compounds

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Infrared spectra were obtained using a schimadzu FT-IR 8201 PC, spectrophotometer (Kyoto, Japan). 1H and 13C neuclear magnetic resonance (NMR) spectra were obtained using a Bruker AC 400 NMR spectrometer (Billerica, MA, USA) at 400 and 100 MHz, respectively. All 1H and 13C nuclear magnetic resonance (NMR) spectral results are recorded as chemical shifts (d) relative to the internal transcranial magnetic stimulation (TMS). Microanalysis was performed by Chemical and Micro-Analytical Services (CMAS), (Highton, VIC, Australia). Melting point determinations were carried out using a Stuart Scientific (SMP3) melting point apparatus (Staffordshire, UK) and all melting points are uncorrected. Reaction courses and product mixtures were routinely monitored by thin-layer chromatography (TLC) on silica gel pre-coated F254 Merck plates (Darmstadt, Germany).
Starting Materials:
The starting reagents, methyl 2-aminobenzoate, picolinoyl chloride, cesium carbonate, triethylamine, dimethylformamide (DMF), acetonitrile, substituted benzylamine, substituted sulphonamide, potassium tert-butoxide, hydrazine hydrate and substituted aryl aldehyde were purchased from Sigma-Aldrich (St. Louis, MO, USA) and were used as received.
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