7697-46-3Relevant articles and documents
Stereochemical modulation of emission behaviour in E/Z isomers of diphenyldipyrroethene from aggregation induced emission to crystallization induced emission
Garg,Ganapathi,Rajakannu,Ravikanth
, p. 19465 - 19473 (2015)
Herein, we report the synthesis, separation and characterisation of the E- and Z-isomers of dipyrrolyldiphenylethene to study their emission behaviour in the aggregation state and solid state. The E-isomer showed pronounced aggregation induced emission (A
K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water
Hunjan, Mandeep Kaur,Laha, Joydev K.
, p. 8437 - 8440 (2021/09/02)
While persulfate activation at room temperature using glucose has primarily been focused on kinetic studies of the sulfate radical anion, the utilization of this protocol in organic synthesis is rarely demonstrated. We reinvestigated selected K2S2O8-mediated known organic reactions that invariably require higher temperatures and an organic solvent. A diverse, mild functionalization and synthesis of heterocycles using the inexpensive oxidant K2S2O8 in water at room temperature is reported, demonstrating the sustainability and broad scope of the method. Unlike traditional methods used for persulfate activation, the current method uses naturally abundant glucose as a K2S2O8 activator, avoiding the use of higher temperature, UV light, transition metals or bases.
Synthesis method of 2-aromatic acyl pyrrole compounds
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Paragraph 0025-0028, (2021/06/12)
The invention relates to the field of organic synthesis, and discloses a synthesis method of 2-aromatic acyl pyrrole compounds, wherein the synthesis method comprises the steps: taking an N-aromatic acyl pyrrole compound as a raw material, and carrying ou
K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins
Laha, Joydev K.,Hunjan, Mandeep Kaur
, p. 664 - 673 (2021/06/03)
The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K2S2O8at 90 C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Br?nsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A4tetraarylporphyrins also in the presence of K2S2O8at 90C. A direct synthesis of A4-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90C is also reported.
Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions
Laha, Joydev K.,Kaur Hunjan, Mandeep,Hegde, Shalakha,Gupta, Anjali
, p. 1442 - 1447 (2020/02/22)
The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.
Rational design of fluorescent probes for targeted: In vivo nitroreductase visualization
Chen, Ji-An,Gao, Jie,Gu, Xianfeng,Li, Mimi,Tan, Jiahui,Yin, Xiaofan,Zhao, Zhen
supporting information, p. 4744 - 4747 (2020/07/13)
Nitroreductase (NTR) has been recognized as a biomarker for identifying the hypoxic status of cancers. Therefore, it is of high scientific interest to design effective fluorescent probes for tracking NTR activity. However, studies on elucidation of the structure-performance relationship of fluorescent probes and those providing valuable insight into optimized probe design have rarely been reported. Three BODIPY based fluorescent probes were made by conjugation of para-, ortho-, and meta-nitrobenzene to the BODIPY core via a thiolether bond, respectively. Our study revealed that the linkage and nitro substituent position significantly influence the capability of nitroreductase detection.
Selective PdII-Catalyzed Acylation of Pyrrole with Aldehydes. Application to the Synthesis of Celastramycin Analogues and Tolmetin
Santiago, Carlos,Rubio, Ibon,Sotomayor, Nuria,Lete, Esther
, p. 4284 - 4295 (2020/05/25)
The PdII-catalyzed C-2 acylation of pyrrole with aldehydes in the presence of TBHP as oxidant has been studied for the synthesis of di(hetero)aryl ketones. The use of 2-pyrimidine as directing group leads to 2-acylpyrroles in moderate to good yields, although 2,5-diacylpyrroles are obtained as by products. This side-reaction could be avoided using 3-methy-2-pyridine as directing group, obtaining selectively 2-acylpyrroles. The reaction has been extended to a series of aromatic and heteroaromatic aldehydes, obtaining the best results with electron rich aromatic aldehydes. The methodology has been applied in the synthesis of pyrrolomycin alkaloid Celastramycin analogues and for an improved synthesis of Tolmetin, a nonsteroidal anti-inflammatory drug.
The Sn(IV)-tetra(4-sulfonatophenyl) porphyrin complexes with antioxidants: Synthesis, structure, properties
Mamardashvili, Galina M.,Lazovskiy, Dmitriy A.,Maltceva, Olga V.,Zh. Mamardashvili, Nugzar,Koifman, Oscar I.
supporting information, p. 468 - 475 (2018/11/23)
Complexes of Sn(IV)-tetra(4-sulfophenyl)porphyrin with antioxidants (methoxydol and ionol) and their precursors (para-cresol and 3-hydroxypyridine) were synthesized. All four complexes were obtained by boiling in aqueous solutions of the p-sulfo substitut
Design of fluorescent probes with optimized responsiveness and selectivity to GSH
Chen, Ji-An,Zhang, Zhen-Yu,Gao, Jie,Tan, Jia-Hui,Gu, Xian-Feng
supporting information, p. 1226 - 1230 (2019/03/27)
We designed and synthesized a series of BODIPY based probes with fast and distinct ratiometric responsiveness for discriminative detection of GSH from Cys and Hcy. The discriminative detection is based on the different products obtained by the SNAr between probes and thiol-containing amino acids. The amino group of the obtained thioether from the reaction with Cys or Hcy but not GSH would trigger an intramolecular nucleophilic substitution through five- or six-membered cyclic transition state, finally yielding an amino substituted derivative. To achieve highly discriminative detection and fast response, a series of structure modifications and improvements have been made by elongating the π-conjugation and introducing electron withdrawing groups, finally affording probe BOD-DBNPF with optimized responsiveness and selectivity. Importantly, BOD-DBNPF was successfully used for the selective detection of GSH from Cys with distinct fluorescent ratiometric responses in living HeLa cells.
Zinc mediated straightforward access to diacylpyrroles
Faye, Djiby,Mbaye, Mbaye Diagne,Coufourier, Sébastien,Lator, Alexis,Dieng, Samba Yandé,Gaillard, Sylvain,Renaud, Jean-Luc
, p. 492 - 499 (2017/05/19)
In this article, we report the preparation of various 2,4- and 2,5-diacylpyrroles via two zinc-mediated acylation reactions of non-protected pyrroles.
