Avance 2 400 mhz

4-Hydroxycoumarin, 3-methyl-1-phenyl-5-pyrazolone, NMSM and all the aldehydes were procured from Sigma-Aldrich. All the solvents were obtained from Merck and Otto Chemie. All the reactions were completed in a REMI 2MLH thermo-mechanical stirrer. TLC analysis was carried out using silica gel GF-254 from SRL (Alfa Aesar). Melting points were obtained on a Stuart digital melting point apparatus (SMP10) and are uncorrected. IR spectra were performed with potassium bromide (KBr) pellets on a PerkinElmer 10.4.00 IR spectrophotometer. ¹H and ¹³C NMR spectral analyses were performed on Bruker (Avance-II 400 MHz), Varian-AS400 NMR, and Bruker Bio Spin GmbH spectrometers using tetramethylsilane (TMS) as the internal standard and DMSO-d₆ or CDCl₃ as the solvent. Crystal data were collected with a Super Nova, single source at offset/far and HyPix3000 diffractometer (CCD) using graphite monochromated MoKα radiation (λ = 0.71073 Å) at 296 K. HRMS spectra were recorded on a high-resolution mass spectrometer XEVO G2-XS QTOF.

Commercially available solvents and chemicals were obtained from suppliers and used to execute this work as received unless otherwise mentioned. All the reactions were performed on a Monowave 300 microwave synthesizer (Anton Paar) by employing a glass vial G10. TLC analysis was performed using silica gel GF-254 from SRL. Stuart digital melting point apparatus (SMP10) was used for the measurement of melting points, which are uncorrected. FTIR spectra were recorded in potassium bromide pellets on a Perkin-Elmer 10.4.00 IR spectrophotometer. ¹H-NMR and ¹³C-NMR spectral analysis were carried out on Bruker (Avance-II 400 MHz, Varian-AS400 NMR) spectrometers using TMS as an internal standard and DMSO-d₆ as a solvent. Crystal data were collected with a SuperNova diffractometer, single source at offset/far, with a HyPix3000 detector (CCD) at 293 K using graphite monochromated MoKα radiation (λ = 0.71073 Å). Elemental analysis was performed on a Perkin-Elmer-2400 CHN/S analyser and Thermo Scientific (FLASH 2000) analyser while high resolution mass spectra were recorded on an ORBITRAP mass analyser (Thermo Scientific, Q Exactive) under electrospray ionisation (ESI) conditions.