6639-57-2Relevant articles and documents
A selective fluorescence probe based on benzothiazole for the detection of Cr3+
Lv, Ren-Gang,Chen, Shu-Wen,Gao, Yan
, p. 389 - 394 (2017)
A novel benzothiazole-functionalized Schiff-base derivative L was prepared and its metal-ion sensing properties were investigated. Sensor L displays selective naked-eye color change from yellow to green in the presence of Cr3+ in aqueous solution at pH 7.2, while other cations do not interfere with the recognition of Cr3+. The proposed mechanism is supported by Job's plot evaluation, IR and ESI-MS studies. The association constant and detection limit of sensor L to Cr3+ are 5.73×104 m-1 and 2.1×10-8 m, respectively. A B3LYP/6-31G (d,p) basis set was employed for optimization of L and L-Cr3+ complex.
The role of weak interactions in self-assembly of supramolecular associations of benzothiazole derivatives and their coordination compounds
García-Ortiz, Alma Lilia,Domínguez-González, Ricardo,Romero-ávila, Margarita,Flores-Pérez, Blas,Guillén, Luis,Castro, Miguel,Barba-Behrens, Norah
, p. 550 - 560 (2018)
New benzothiazole derivatives and their transition metal coordination compounds were synthesized and structurally characterized. The participation of weak interactions, as H-bonding, π-stacking, O → S, N → S and S lone pair···π on the stabilization of their supramolecular assemble was analyzed. The bis-benzothiazole (ebbtz) derivative was obtained from the reaction of benzothiazole-2-carboxaldehyde and ethylenediamine. When reacting this ligand with copper(II) chloride, an electrophilic addition of methanol, as a methoxy group, gave place to the amino ether derivative on the coordination compound [Cu(MeO-ebbtz)Cl]Cl·4H2O. The supramolecular arrangement of this compound is stabilized by H-bonding, O → S, N → S, lp(S)···π and π-stacking interactions. Whereas, from the reaction in situ of benzothiazole-2-carboxaldehyde, ethylenediamine and copper(II) bromide, the polymeric [Cu2(μ-Br)3(ebtz)Br]n compound was obtained. In this compound, the copper(II) atoms present two different geometries, tetrahedral and octahedral, where a 3D assembly is driven by lp(S)···π and π···π stacking. Two isostructural [M(H2O)2(CH3OH)4]·2(prbtz) (M = CoII and NiII) compounds and a polymeric sodium complex were obtained with 3-(benzothiazol-2-ylthio)-1-propanesulfonate (prbtz). In the [Na2(prbtz)2(H2O)2μ-(H2O)]n polymer, the prbtz? is bound to the metal ion in a bent conformation, presenting a supramolecular arrangement stabilized by H-bonding, N → S, T-shape and lp(S)···π interactions. On the other hand, in the [M(H2O)2(CH3OH)4]·2(prbtz) compounds, prbtz? co-crystallized, presenting an extended conformation, mainly with lp(S)···π interactions. Additionally, theoretical calculations on the association between two ebbtz molecules, were performed. The results indicate that these molecules have a binding energy of 79.49 kJ/mol promoted by lp(S)···π and π···π stacking interactions, taking place at the frontier LUMO and HOMO molecular orbitals.
Iodine-catalyzed oxidative annulation: Facile synthesis of pyrazolooxepinopyrazolones: Via methyl azaarene sp3C-H functionalization
Zhang, Xin-Ke,Miao, Xiao-Yu,Zhou, Yu,Wang, Yu-Mei,Song, Ying-Chun,Liu, Hang,Xiong, Yi-Lu,Li, Ling-Yu,Wu, An-Xin,Zhu, Yan-Ping
supporting information, p. 1236 - 1242 (2022/02/19)
An iodine-catalyzed methyl azaarene sp3 C-H functionalization has been developed for the synthesis of a seven-membered O-heterocyclic architecture containing three different heterocyclic aromatic hydrocarbons. This method can be applied to a wide range of substituted methyl azaarenes and diverse 2,4-dihydro-3H-pyrazol-3-ones, and brings about the efficient preparation of 2,9-dihydrooxepino[2,3-c:6,5-c′]dipyrazol-3(7H)-ones in high yields with the merits of low catalyst loading, good functional group tolerance and metal-free conditions.
Synthesis of new Zn (II) complexes for photo decomposition of organic dye pollutants, industrial wastewater and photo-oxidation of methyl arenes under visible-light
Ahemed, Jakeer,Bhongiri, Yadagiri,Chetti, Prabhakar,Gade, Ramesh,Kore, Ranjith,Pasha, Jakeer,Pola, Someshwar,Rao D, Venkateshwar
, (2021/07/28)
Synthesis of new Schiff's base Zn-complexes for photo-oxidation of methyl arenes and xylenes are reported under visible light irradiation conditions. All the synthesized new ligands and Zn-complexes are thoroughly characterized with various spectral analyses and confirmed as 1:1 ratio of Zn and ligand with distorted octahedral structure. The bandgap energies of the ligands are higher than its Zn-complexes. These synthesized new Zn(II) complexes are used for the photo-fragmentation of organic dye pollutants, photodegradation of food industrial wastewater and oxidation of methyl arenes which are converted into its respective aldehydes with moderate yields under visible light irradiation. The photooxidation reaction dependency on the intensity of the visible light was also studied. With the increase in the dosage of photocatalyst, the methyl groups are oxidized to get aldehydes and mono acid products, which are also identified from LC-MS data. Finally, [Zn(PPMHT)Cl] is with better efficiency than [Zn(PTHMT)Cl] and [Zn(MIMHPT)Cl] for oxidation of methyl arenes is reported under visible-light-driven conditions.
Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System
Hu, Qi-Qi,Gao, Yan-Ting,Sun, Jia-Chen,Gao, Jing-Jing,Mu, Hong-Xiao,Li, Yi-Ming,Zheng, Ya-Nan,Yang, Kai-Rui,Zhu, Yan-Ping
supporting information, p. 9000 - 9005 (2021/11/24)
An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.
[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization
Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip
supporting information, p. 890 - 895 (2021/02/01)
A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.
Efficient synthesis of acrylates bearing an aryl or heteroaryl moiety: One-pot method from aromatics and heteroaromatics using formylation and the horner-wadsworth-emmons reaction
Yasukata, Tatsuro,Matsuura, Takaharu
, p. 527 - 533 (2021/03/22)
Acrylates bearing an aryl or heteroaryl moiety were efficiently prepared by a one-pot process employing a sequence of lithiation, formylation and the Horner-Wadsworth-Emmons reaction starting from aromatic and heteroaromatic compounds. This method can efficiently introduce an acrylate moiety into aromatic and heteroaromatic compounds.
Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines
Wu, Yue,Guo, Peng,Chen, Long,Duan, Weijie,Yang, Zengzhuan,Wang, Tao,Chen, Ting,Xiong, Fei
, p. 3271 - 3274 (2021/04/07)
The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.
A simple but sensitive and efficient fluorescent probe for “turn-on” sensing of ClO?
Cui, Chuanyang,Cui, Yu,Dong, Xiaoling,Huang, Xin,Li, Yexin,Shi, Wendi,Sun, Guoxin,Wang, Xue,Xie, Hangxin,Yan, Mei,Yang, Xiaofeng
supporting information, (2020/05/08)
A simple but sensitive and efficient fluorescent probe YXF for “turn-on” detecting ClO? had been developed. For compound YXF, the benzothiazole unit was the efficient fluorophore, and the C[dbnd]N unit was the recognition site for ClO?. It could detect ClO? with a high selectivity and sensitivity over other 29 kinds of common analytes including some reactive oxygen molecules. After addition of 30 equiv. NaClO to the solution of YXF, the fluorescent intensity at 452 nm enhanced with an approximately 37-fold within seconds. The fluorescence intensity of the reaction between YXF and NaClO showed a good linearity in the NaClO concentration range of 1–180 μM and YXF had a low detection limit of 1.8 × 10?8 M. In addition, NaClO-promoted oxidation cleavage of C[dbnd]N unit of probe YXF was verified by HR-MS and NMR spectrometry analysis. Moreover, probe YXF could be successfully applied for detection of ClO? concentration in several tap water and 84 disinfectant samples.
Synthesis of silyl formates, formamides, and aldehydesviasolvent-free organocatalytic hydrosilylation of CO2
Ema, Tadashi,Hasegawa, Jun-Ya,Hiyoshi, Mahoko,Murata, Takumi,Ratanasak, Manussada
supporting information, p. 5783 - 5786 (2020/06/03)
Carbon dioxide (CO2) was used as a C1 source to prepare silyl formates, formamides, and aldehydes. Tetrabutylammonium acetate (TBAA) catalyzed the solvent-freeN-formylation of amines with CO2and hydrosilane to give formamides including Weinreb formamide, Me(MeO)NCHO, which was successively converted into aldehydes by one-pot reactions with Grignard reagents.
