Avance av 300 mhz

Reactions were carried out under an argon atmosphere using standard Schlenk line techniques. Solvents were obtained from a Solvent Purification System from Innovative Technology Inc. NaB₃H₈·3(C₄H₈O₂) was purchased from Katchem spol. s r. o., and used as received. The deuterated solvent CD₂Cl₂ was deaerated, following freeze–pump–thaw methods, and dried over 3 Å molecular sieves.
Infrared spectra were recorded on a Perkin-Elmer 100 spectrometer, using a Universal ATR Sampling Accessory. Solution NMR spectra were recorded on Bruker Avance AV 300-MHz, AV 400-MHz and AV 500-MHz spectrometers, using ¹¹B, ¹¹B-{¹H}, ¹H, ¹H-{¹¹B}, ¹H-{¹¹B(selective)}, ¹H-³¹P-HMBC and ¹H-¹H-COSY techniques. The ¹H NMR chemical shifts were measured relative to the partially deuterated solvent peaks but are reported in ppm relative to tetramethylsilane. ¹¹B chemical shifts are quoted relative to [BF₃·OEt₂].

Chemicals were purchased from Sigma Aldrich (St. Louis, MO, USA) and Alfa Aesar (Ward Hill, MA, USA). Melting points were taken on Griffin and George melting point apparatus using the open capillary tube method and were reported as uncorrected. Infrared spectra were recorded in KBr on a Jasco-320-A spectrophotometer. ¹H-NMR signals were recorded on AVANCE AV-300 MHz, AVANCE AV-400 MHz, or AVANCE AV-500 MHz while ¹³C-NMR spectra were taken on a Bruker AVANCE AV-75 MHz, AVANCE AV-100 MHz and AVANCE AV-125 MHz spectrometer. EIMS signals were recorded on JEOL MS 600H-1 spectrometer. 5-[2-(4-Chlorophenoxy)propan-2-yl]-1,3,4-oxadiazol-2-thiol 1 [29 ] and aromatic N-substituted-2-bromoacetamides (2a–2i) were synthesized by previously reported methods with slight modifications [12 ].