General procedure for the synthesis of indolizine compoundsĪ mixture of 0.1 mmol of the iminophosphorane intermediate (1-10) (Scheme 1 and Table 1) and 0.1 mmol of the corresponding 2,3-thiophenecarboxaldehyde in 2 mL of xylene was refluxed for 48 h. Chemical shifts for 13C NMR spectra are recorded in parts per million from tetramethyl silane using the central peak of CDCl 3 ( δ = 77.16 ppm) as the internal standard, all 13C NMR spectra were obtained with complete proton decoupling. The Hydrogen Nuclear Magnetic Resonance ( 1H NMR) and Carbon-13 Nuclear Magnetic Resonance ( 13C NMR) spectra were recorded on a Bruker 300 Megahertz (MHz) spectrometer operating at observation frequency of 300 MHz for 1H and 75 MHz for 13C, also was used a Varian 500MHz spectrometer operating at observation frequency of 500 MHz for 1H and 125 MHz for 13C chemical shifts for hydrogen are given in parts per million (ppm) relatives to tetramethyl silane (TMS) using the central peak of chloroform (CHCl 3) ( δ = 7.26 ppm) as internal standard. Melting points were determined with a Kofler Hot Stage Apparatus and were not corrected. Anhydrous solvents (ethanol, toluene) and reagents were used as from commercial bottles. This coupling is leading to the formation of the molecules derived from alkaloids core, specifically that of indolizines.Īll reactions were run under nitrogen atmosphere without moisture. In this context, we developed in this study a new strategy toward the title compounds using the iminophosphorane intermediates and their reaction with 2,3-thiophenedicarboxaldehyde. The indolizine containing molecules then became a challenging synthetic target and several strategic routes to build completely new structures in this family or simply to obtain known molecules in reduced number of steps or avoiding expensive reagents were proposed. Indolizine derivatives obtaining have become an important topic in organic synthesis. The indolizines nuclei are present for example in more complex molecules with potent analgesic, anti-inflammatory, antimicrobial, hypoglycemic, CNS depressor, antioxidant and anti- cancerogenic activities, inhibitors that modulate gene transcription. Indolizine synthesis is of growing interest in medicinal chemistry. In this context, synthesis of indolizines compounds has been reported using ingenious and sophisticated pyridine starting strategies. In particular, the development of new routes to achieve both, new and improved synthesis of these products, is in constant demand. Synthetic organic chemistry presents a significant and still growing number of reports focused on the synthesis of molecules with biological and pharmaceutical potential.
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