Mat 311a

Starting materials and reagents were purchased from Sigma-Aldrich and used without purification. Melting points measurement was carried out by a Gallen lamp melting point apparatus and are uncorrected. Reactions progress was monitored by TLC (Merck, Germany), the spots were detected by exposure to UV lamp at λ 254 nm. IR spectra were recorded by pye Unicam SP 1000 IR spectrophotometer using KBr discs and expressed in wavenumber (cm⁻¹). ¹H and ¹³C NMR spectra were recorded with Bruker Advance 400 spectrophotometer operating at 400 MHz and 100 MHz, respectively and the chemical shifts were given in δ as parts per million (ppm) downfield from tetramethylsilane (TMS) as internal standard. The mass spectra were recorded on Varian MAT 311-A (70 e.v.).
The previously reported compounds 2,3-dihydrophthalazine-1,4-dione 2³⁴ , 1,4-dichlorophthalazine 3³⁵ and 1-chloro-4-hydrazineylphthalazine 4³⁵ , 6-chloro-3-propyl-[1, 2, 4]triazolo[3,4-a]phthalazine 5⁴⁹ (link), and N-aryl-2-chloroacetamide 11a-c⁵⁰ were synthesised following the described procedures.

All starting compounds were purchased from Aldrich, Alfa Aesar and TCI. The known compounds 1 n–q were prepared according to literature procedures.[¹⁰, ⁴⁷] The following instruments were applied for this study: melting points (uncorrected), Gallenkamp; IR spectra, Perkin‐Elmer Spectrum One FT‐IR spectrophotometer with ATR sampling unit; nuclear magnetic resonance spectra, BRUKER Avance 300 spectrometer; chemical shifts are given in parts per million (δ) downfield from tetramethylsilane as internal standard; mass spectra, Varian MAT 311 A (EI), UPLC/Orbitrap (ESI); microanalyses, Perkin‐Elmer 2400 CHN elemental analyzer. All tested compounds were >95 % pure by elemental analysis.

Starting compounds and reagents were obtained from Aldrich, TCI, and Alfa Aesar. The already published compounds 1A, 1B, 2B, 2O, and 2R were prepared as described^{[5 (link),6 (link),9 ,14 ]}. For compound analysis, the following instruments were used: Gallenkamp for melting points (uncorrected); Perkin-Elmer Spectrum One FT-IR spectrophotometer (ATR) for IR spectra; BRUKER Avance 300 spectrometer for nuclear magnetic resonance spectra; chemical shifts were expressed as ppm (parts per million, δ) downfield from TMS (tetramethylsilane) as the internal standard; Varian MAT 311A (EI) and UPLC/Orbitrap (ESI-HRMS) for mass spectra; Perkin-Elmer 2400 CHN elemental analyzer for elemental analyses (microanalyses), and compounds were > 95% pure as to elemental analysis.

Melting points were determined on the electrothermal apparatus and were not corrected. ¹H and ¹³C NMR spectra were recorded on AC 250 MHz and 400 MHz Bruker instruments. The chemical shifts (δ) are provided in ppm relative to tetramethylsilane (TMS) as an internal standard. Mass spectra were recorded on Perkin Elmer Sciex API 100 and Varian MAT 311A instruments (Paul Sabatier University in Toulouse).

Melting points were measured with a Gallenkamp apparatus (uncorrected, Electrothermal, Stone, UK). IR spectra were obtained from a PerkinElmer Spectrum One FT-IR spectrophotometer with ATR (attenuated total reflection) sampling unit. NMR spectra were obtained from a BRUKER Avance 300 spectrometer and chemical shifts (δ) are given in parts per million downfield from tetramethylsilane as the internal standard. The ¹H NMR signals are described as s (singlet), br s (broad singlet), d (doublet), dd (doublet of doublets), t (triplet) and m (multiplet). Coupling constants J (in Hz) are provided. Mass spectra were measured on a Varian MAT 311A (EI). For HRMS (high-resolution mass spectrometry) analyses, an UPLC/Orbitrap system in ESI mode was applied. Microanalyses were obtained from an Elementar Unicube and test compounds were >95% pure by elemental analyses.

SMP 30 apparatus was applied to record the melting point of the obtained congeners and the results were uncorrected. The progress of the synthetic steps was checked by the pre-coated silica gel plates (Merck 60 F₂₅₄, Darmstadt, Germany) followed by visualising the applied spots with a UV lamp (254 nm). ¹H NMR and ¹³C NMR (400 and 100 MHz, respectively) spectra were carried out by a Bruker NMR spectrometer (Billerica, MA). DMSO-d₆ was the solvent used in the NMR analysis. While mass spectra were obtained using Varian MAT 311-A (70 eV).