Synthesis and optical properties of two novel stilbene derivatives containing 1,3,4-oxadiazole moiety

Synthetic approaches toward stilbenes and their related structures

“…Zhu et al [43] synthesized conjugated stilbenes carrying an oxadiazole moiety 107 to study their optical properties. Oxadiazole 104 was formed in 60% yield by direct reaction of p-toluic acid 102 with hydrazine hydrate 103 in the presence of polyphosphoric acid.…”

“…The non-availability of naturally occurring stilbenes in sufficient quantities dictated the development of synthetic methodologies for their preparation at large scale [3] such as Wittig or Horner-Wadsworth-Emmons (HWE) olefination, Perkin aldol condensation, transition metal coupling, i.e., Mizoroki-Heck, Negishi, Stille, Sonogashira, Suzuki-Miyaura, Grubbs & McMurry, Knoevenagel-Doebner, Ramberg-Bucklund reactions [7,34,38,39]. Stilbene derivatives also show industrial applications in electrochemical, dyes, dye laser, coloring textiles, organic LED, fluorescent and optical brightners [40][41][42][43]. Likhitwitayawuid identified dimeric stilbenes as tyrosinase inhibitor [44], whereas Momotake and Arai wrote a review on photochemistry and photophysics of stilbene dendrimers and related compounds [45].…”

Synthesis, Crystal Structure and Antibacterial Activity of 2-(p-Tolyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole

“…During the last few decades, considerable attention has been devoted to the synthesis of 1,3,4-oxadiazole derivatives which have been found to exhibit diverse biological activities such as antibacterial 1,2 , antifungal 3,4 , antiinflammatory 5 , analgesic 6 , anticonvulsant 7 and insecticidal activities [8][9][10] . Moreover, substituted 1,3,4-oxadiazoles also revealed anticancer 11,12 and tyrosinase inhibitory activities 13,14 . In this paper, 2-(p-tolyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole was efficiently synthesized by the condensation of 4-methylbenzohydrazide and 3,4,5-trimethoxy-benzaldehyde in ethanol solution with chloramine-T. Its crystal structure was determined by X-ray single crystal diffraction analysis.…”

Synthesis, photophysical properties, and application of optical brighteners based on stilbene‐oxadiazole derivatives

“…These compounds are also well known for their considerable biological and medical activities [5][6][7][8][9]. With the presence of an uninterrupted system of conjugated double bonds and incorporation of new chemical substituents to the fluorophore, the FWAs show high fluorescence activity, which in turn improves their potential applications [13][14][15]. With the presence of an uninterrupted system of conjugated double bonds and incorporation of new chemical substituents to the fluorophore, the FWAs show high fluorescence activity, which in turn improves their potential applications [13][14][15].…”