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Content available remote Synthesis and structure of new 3,7,10-substituted-phenothiazine derivatives
The synthesis of new 3,7-dibromophenothiazine derivatives bearing bromoalkyl, mercaptoalkyl and alkylthioacetate groups on the N atom at position 10 is reported. The Suzuki coupling reaction of one of these derivatives via the bromine atoms at positions 3 and 7 with bromothiophene derivatives is also discussed. [...]
Pd-catalyzed C-C bond forming reactions have attracted huge interest not only among the synthetic organic chemists but researchers of various disciplines for over two decades because a large panorama of value added organic target molecules can be designed employing this synthesis protocol. Richard F. Heck, Ei-ichi Negishi and Akira Suzuki have been awarded the Nobel Prize in Chemistry 2010 for their pioneering works on these palladiumcatalyzed cross-coupling reactions in organic synthesis. More greener and eco-friendly synthetic conditions together with the recyclability of the Pdcatalyst have been continuously hunted over the years. It is essential to know the different steps and mechanism involved in these C-C coupling reactions together with the active Pd-sites present at the catalytic surfaces. In this review we have focused on discussing various protocols involved in the C-C coupling reactions and gradual developments in Pd-grafted functionalized mesoporous materials. Recyclability and sustainability of the catalyst along with their surface modification strategies have been discussed. Catalytic efficiency of these functionalized mesoporous materials largely depends on strong binding of the Pd-sites with the support matrix. Thus, discussion on different types of supports has also been made.
Content available remote Synthesis of Xenbucin using Suzuki reaction catalyzed by Pd/C in water
Xenbucin 1, an analgesic drug, was synthesized in 4 steps using two different routes. The biaryl fragment could successfully be produced via a Pd/C catalysed Suzuki coupling in water using sodium tetraphenylborate as a phenylation reagent. Overall yields of the routes were 36% and 59%, respectively. [...]
Biaryls are the potential source of synthetic drugs. The present study describes the synthesis of a series of functionalized biphenyl derivatives (3a-3g) using Pd-catalyzed Suzuki coupling reaction. The experimental results revealed the facile synthesis of biphenyl derivatives (3a-3g) with notably high yield (80-88 %). Density functional theory (DFT) studies were performed by Gaussian 09 software in order to rationalize the selectivity of coupling at C-Br bond instead of C-Cl bond. In addition of synthesis, the biological activities (biofilm inhibition, hemolytic and anti-thrombolytic) of these novel compounds were investigated. These results exhibited good biofilm inhibition (5.86-65.8 %), hemolytic (1.32-30.1 %) and anti-thrombolytic activities (9.64-42.5 %), indicating the potential use of these compounds for pharmaceutical applications.
The potential for expanding the variety of catalytic methods for carbon-carbon bond formation is being currently explored in many research centres all over the world. An increasing use of selected d-block metals as catalysts in the synthesis has brought new methods of functionalization of organic and organometallic compounds of great importance for development of polymer chemistry and organic chemical technology [5, 6]. This work describes very precise and controlled catalytic transformations as useful tools for the synthesis of new E-conjugated organic, organosilicon molecular and polymeric compounds. The combination of Suzuki-Miyaura coupling and silylative coupling reactions as a simple and efficient method is established for designing new E-stereoregular hybrid materials in the presence of well-defined transition metal (TM) catalysts. All presented compounds can be interesting precursors for a further functionalization that may significantly increase the possibility of their application in the design and synthesis of new functional materials.
A convenient and high yield synthetic route to arylene derivatives was reported and their electrochemical character was shown by properties of polymer with alternate arylene and bispyridine, bisthiophene, bisfurane and bisthiazole units. Polmerization is processed as two steps bielectronic oxidation of molecules. In monoelectronic oxidation stableradical cation is formed with spin located on phenothiazine. The electrochemical properties of polymer are dependent on film thick ness deposited on electrode. In the case of the thin layers one can observe characteristic redox couple of phenothiazine oxidation to radical cation. Analysis of polymer behaviour and results of spectrochemical measurements point on mixed type of electroconducting.
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