26211-73-4Relevant academic research and scientific papers
3-benzoyl-2-methylindole
Martinez-Alcazar, M. Paz,Fonseca, Isabel,Cano, Felix H.,Gonzalo Rodriguez,Urrutia, Anahi
, p. 1345 - 1347 (1997)
The crystal and molecular structure of C16H13NO has been determined. Bond lengths and angles are within normal ranges and molecules are held together in the crystal by intermolecular N-H...O hydrogen bonding.
Lithium-Promoted Cycloaddition of Indole-2,3-dienolates and Carbon Disulfide as a One-Pot Route to Thiopyrano[4,3- b]indole-3(5 H)-thiones
Suzdalev, Konstantin F.,Vyalyh, Julia V.,Tkachev, Valery V.,Lysenko, Ekaterina A.,Burov, Oleg N.,Lisovin, Anton V.,Kletskii, Mikhail E.,Kurbatov, Sergey V.
, p. 11698 - 11707 (2021/08/24)
A new approach for the annulation of a thiopyrane ring to an indole core under mild conditions was developed. Treating 2-methyl-3-acylindoles with lithium diisopropyl amide leads to the elimination of a proton from the 2-methyl group. The lithium indole-2,3-dienolates obtained were found to react with CS2 to give the corresponding thiopyrano[4,3-b]indole-3(5H)-thiones. The mechanism represents a stepwise addition through ion-pair formation, according to PCM/B3LYP/6-311++G**, PBE1PBE/6-311++G**, and MP2//HF/6-311++G*? quantum chemical calculations. AIM calculations revealed the essential role of the Li atom at all stages of the process.
Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions
Hunjan, Mandeep Kaur,Laha, Joydev K.,Tinwala, Ummehani
, p. 22853 - 22859 (2021/12/24)
Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. This journal is
K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water
Hunjan, Mandeep Kaur,Laha, Joydev K.
supporting information, 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 of 3-acylindoles: via copper-mediated oxidative decarbethoxylation of ethyl arylacetates
Jaiswal, Anjali,Sharma, Anup Kumar,Singh, Krishna Nand
supporting information, p. 1623 - 1628 (2020/03/06)
An efficient regioselective C-3 acylation of free indoles (N-H) has been accomplished via oxidative decarbethoxylation of easily available ethyl arylacetates using Cu(OAc)2 and KOtBu in DMSO.
Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions
Laha, Joydev K.,Kaur Hunjan, Mandeep,Hegde, Shalakha,Gupta, Anjali
supporting information, 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.
Selective C-H acylation of indoles with α-oxocarboxylic acids at the C4 position by palladium catalysis
Zhang, Jitan,Wu, Manyi,Fan, Jian,Xu, Qiaoqiao,Xie, Meihua
supporting information, p. 8102 - 8105 (2019/07/15)
The first Pd-catalyzed direct C-H acylation of indoles at the C4 position with α-oxocarboxylic acids using a ketone directing group is described. This reaction exhibits high regioselectivity with the tolerance of a wide scope of functional groups to afford diverse acylated indoles in moderate-to-good yields. The control experiments evidence the generation of acyl radicals via K2S2O8 promoted decarboxylation of α-oxocarboxylic acids and the involvement of a PdII/PdIV catalytic cycle. Importantly, the synthetically useful selectivity observed might be applied to prepare indole derivatives with anti-tumor activity as tubulin inhibitors.
Decarboxylative acylation of: N -free indoles enabled by a catalytic amount of copper catalyst and liquid-assisted grinding
Yu, Jingbo,Zhang, Chao,Yang, Xinjie,Su, Weike
supporting information, p. 4446 - 4451 (2019/05/16)
A facile decarboxylative acylation of N-free indoles with α-ketonates via liquid-assisted grinding was reported. The reaction requires only a catalytic amount of Cu(OAc)2·H2O in combination with O2 as the terminal oxidant to give various 3-acylindoles with high efficiency. Additionally, this new methodology was applicable to a gram-scale synthesis.
Synthesis of indoles and quinazolines via additive-controlled selective C-H activation/annulation of N -arylamidines and sulfoxonium ylides
Lai, Ruizhi,Wu, Xiaohua,Lv, Songyang,Zhang, Chen,He, Maoyao,Chen, Yuncan,Wang, Qiantao,Hai, Li,Wu, Yong
, p. 4039 - 4042 (2019/04/10)
Selective synthesis of indole and quinazoline products was achieved through a precise control of the C-H activation/annulation by changing the additives from NaOAc to CuF2/CsOAc. This strategy constructs indole and quinazoline scaffolds efficie
A through C - H activation synthetic 3 - acylated indole derivatives (by machine translation)
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Paragraph 0013; 0014, (2019/02/10)
The invention discloses a to [...] and α - carbonyl sulfur ylide as raw materials, through C - H activation reaction synthesis of indole derivatives of the new method. The method of the invention can quickly and efficiently synthesizing 3 bit acceleration
