5344-90-1Relevant academic research and scientific papers
Design and Photophysical Studies of Acridine-Based RuIIComplexes for Applications as DNA Photoprobes
Deraedt, Quentin,Marcélis, Lionel,Auvray, Thomas,Hanan, Garry S.,Loiseau, Frédérique,Elias, Benjamin
, p. 3649 - 3658 (2016)
A series of new extended planar aromatic ligands based on an acridine core (dpac = dipyrido[3,2-a:2′,3′-c]acridine; dpacF2= 7,8-difluorodipyrido[3,2-a:2′,3′-c]acridine; dpacF4= 6,7,8,9-tetrafluorodipyrido[3,2-a:2′,3′-c]acridine) and their respective RuIIcomplexes were synthesized and extensively studied. The photophysical and theoretical studies revealed that Ru-DPAC and Ru-DPACF2allow emission from a3MLCTphen/dpacexcited state at 597 and 604 nm, respectively, whereas the lowest excited state for Ru-DPACF4shifts from a bright3MLCTphen/dpacstate towards a poorly luminescent3MLCTdpacstate (λem= 609 nm) owing to the formation of hydrogen bonds with water molecules in the excited state. These complexes exhibit up to sevenfold luminescence enhancement in the presence of complementary and mismatched DNA, demonstrating a strong binding to polynucleotides. The results emphasize the interest in RuIIcomplexes bearing acridine derivatives as DNA interacting agents as a complement to the well-known phenazine-based derivatives.
Magnetic ethyl-based organosilica supported Schiff-base/indium: A very efficient and highly durable nanocatalyst
Mirbagheri, Reza,Elhamifar, Dawood
, p. 783 - 791 (2019)
In the present study a novel core-shell structured magnetic bifunctional organosilica was prepared through modification of Fe3O4 nanoparticles with a mixture of bis(triethoxysilyl) ethane (BTEE) and 3-aminopropyltrimethoxysilane (APTES) followed by treatment with 2-hydroxybenzaldehyde. This nanomaterial was applied as efficient support for immobilization of indium chloride. The prepared nanomaterial was denoted as Fe3O4@BOS@SB/In and characterized using Fourier transform infrared (FT-IR) spectroscopy, thermal gravimetric analysis (TGA), energy-dispersive X-ray (EDX) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), vibrating sample magnetometer (VSM) and powder X-ray diffraction (PXRD). The Fe3O4@BOS@SB/In was successfully applied as a powerful catalyst for green reduction of nitrobenzenes in water at room temperature. This catalyst was recovered and reused several times without significant decrease in efficiency and stability.
Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines
Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju
supporting information, p. 1915 - 1923 (2021/02/06)
Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.
Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water
Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein
, p. 3289 - 3312 (2021/05/11)
Developing and/or modifying fundamental chemical reactions using chemical industry-favorite heterogeneous recoverable catalytic systems in the water solvent is very important. In this paper, we developed convenient, green, and efficient approaches for the chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes in the presence of the recoverable heterogeneous carbon-supported palladium (Pd/C) catalytic system in water. The utilize of the simple, effective, and recoverable catalyst and also using of water as an entirely green solvent along with relatively short reaction times and good-to-excellent yields of the desired products are some of the noticeable features of the presented synthetic protocols. Graphic abstract: [Figure not available: see fulltext.].
Electrochemical access to benzimidazolone and quinazolinone derivatives: Via in situ generation of isocyanates
Saha, Debarshi,Taily, Irshad Maajid,Naik, Sumitra,Banerjee, Prabal
, p. 631 - 634 (2021/01/29)
Isocyanates are the key intermediates for several organic transformations towards the synthesis of diverse pharmaceutical targets. Herein, we report the development of an oxidant-free protocol for electrochemical in situ generation of isocyanates. This strategy highlights expedient access to benzimidazolones and quinazolinones and eliminates the need for exogenous oxidants. Furthermore, detailed mechanistic studies provide strong support towards our hypothesis of in situ isocyanate generation. This journal is
Transition metal-free approach to azafluoranthene scaffolds by aldol condensation/[1+2+3] annulation tandem reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes
Dong, Penghui,Majeed, Kashif,Wang, Lingna,Guo, Zijian,Zhou, Fengtao,Zhang, Qiuyu
supporting information, p. 4855 - 4858 (2021/05/25)
A transition metal-free aldol condensation/[1+2+3] annulation reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes has been developed for the general synthesis of azafluoranthenes. This domino reaction enables successive formation of three new bonds and two rings from readily accessible starting materials in a single operation. Furthermore, this methodology can also be utilized to construct chromeno[4,3-c]pyridines and benzo[c][2,6]naphthyridines in moderate yields.
Construction of a benzo[b]azepine skeleton through decarboxylative ylide [6+1] annulations with modified vinyl benzoxazinanones
Li, Qing-Zhu,Jia, Zhi-Qiang,Chen, Lin,Zhang, Xiang,Leng, Hai-Jun,Zeng, Rong,Liu, Yan-Qing,Zou, Wen-Lin,Li, Jun-Long
supporting information, p. 814 - 818 (2021/02/16)
A Lewis acid-promoted [6+1] annulation between sulfur ylides and modified vinyl benzoxazinanones was described. In this reaction, the newly designed vinyl benzoxazinanones could serve as a novel six-atom synthon, and the key to success is the installation of an electron-withdrawing group on the alkene moiety of the benzoxazinanones. A broad range of substrates are compatible with this mild reaction system, thereby providing a facile and practical approach for constructing a benzo[b]azepine skeleton.
Access to 5,6-Spirocycles Bearing Three Contiguous Stereocenters via Pd-Catalyzed Stereoselective [4 + 2] Cycloaddition of Azadienes
Fairuz Binte Sheikh Ismail, Siti Nur,Yang, Binmiao,Zhao, Yu
supporting information, p. 2884 - 2889 (2021/05/05)
We present herein a highly diastereo- and enantioselective Pd-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes with vinyl benzoxazinanones, which represents a rare highly stereoselective cycloaddition of this class of fused azadienes as a two-atom synthon. The use of a phosphoramidite ligand bearing a chiral secondary amine with a simple biphenyl backbone proved to be the key to construct the novel spirocyclic tetrahydroquinoline scaffold containing three contiguous stereocenters as a single diastereomer in high enantioselectivity.
Metal-Free C-C/C-N/C-C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[ b]indolines
Lázaro-Milla, Carlos,Yanai, Hikaru,Almendros, Pedro
supporting information, p. 2921 - 2926 (2021/05/05)
A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.
A Convenient Formal [4+2] Heterocylization Route to Bis(triflyl)tetrahydroquinolines
Lázaro-Milla, Carlos,Almendros, Pedro
supporting information, p. 13534 - 13538 (2021/08/13)
We report the sustainable and efficient synthesis of a new type of quinoline derivatives bearing one or two SO2CF3 groups. The protocol is metal-, catalyst- and irradiation-free, involves the use of readily available and stable precursors, and avoids the formation of side products. Also, the mild conditions of the process allow the tolerance of a wide range of functional groups.
