55276-35-2Relevant academic research and scientific papers
Photo-redox catalyzed dehydrazinative acylation of N-heterocycles: Via Minisci reaction
Hafeez, Saira,Saeed, Aamer
, p. 38683 - 38689 (2021/12/20)
Visible light-induced acylation of heteroaromatic compounds have been achieved using benzoyl hydrazides as an efficient acyl source under mild reaction conditions. The photo-redox catalyzed oxidative cleavage of hydrazides leads to in situ formation of ac
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.
Alkanoylation of quinazoline by nucleophilic aromatic substitution: Combined experimental and computational study
Suzuki, Yumiko,Iwata, Naoto,Dobashi, Kohei,Takashima, Ryo,Arulmozhiraja, Sundaram,Ishitsubo, Erika,Matsuo, Naoya,Tokiwa, Hiroaki
, p. 392 - 400 (2017/12/28)
A combined experimental and computational study on the key intermediates of NHC-catalyzed acylation reaction, Breslow intermediates (BIs), has been conducted in order to achieve a direct nucleophilic alkanoylation of N-heterocycles. Various BI precursors
Visible-Light-Triggered, Metal- and Photocatalyst-Free Acylation of N-Heterocycles
Guillemard, Lucas,Colobert, Fran?oise,Wencel-Delord, Joanna
supporting information, p. 4184 - 4190 (2018/09/25)
A photoinduced acylation of N-heterocycles is explored. This visible-light triggered reaction occurs not only under extremely mild reaction conditions, but also does not require the presence of a photosensitizer. The mechanistic studies suggest formation of EDA complexes prompt to harness the energy from visible-light. Compatibility with a large panel of α-keto acids as acyl precursors and an array of N-heterocycles clearly showcase the synthetic potential of this handy and green acylation protocol. (Figure presented.).
Photoredox-Catalyzed Decarboxylative C-H Acylation of Heteroarenes
Jia, Wei,Jian, Yong,Huang, Binbin,Yang, Chao,Xia, Wujiong
supporting information, p. 1881 - 1886 (2018/08/28)
A mild, environmentally friendly, and regioselective acylation of heterocycles with inexpensive carboxylic acids is reported via photoredox catalysis. The strategy is highlighted with good functional group tolerance and substrate scope which could rapidly
Synthesis and structure-activity relationship study of 1-phenyl-1-(quinazolin-4-yl)ethanols as anticancer agents
Kuroiwa, Kenta,Ishii, Hirosuke,Matsuno, Kenji,Asai, Akira,Suzuki, Yumiko
supporting information, p. 287 - 291 (2015/03/30)
A quinazoline derivative PVHD121 (1a) was shown to have strong antiproliferative activity against various tumor-derived cell lines, including A549 (lung), NCI-H460 (lung), HCT116 (colon), MCF7 (breast), PC3 (prostate), and HeLa (cervical) cells with IC50 values from 0.1 to 0.3 M. A structure-activity relationship (SAR) study at the 2- and 4-position of the quinazoline core lead to the discovery of more potent anticancer agents (14, 16, 17, 19, 24, and 31). The results of an in vitro tubulin polymerization assay and fluorescent-based colchicine site competition assay with purified tubulin indicated that 1a inhibits tubulin polymerization by binding to the colchicine site.
Pd(0)-catalyzed benzylic arylation-oxidation of 4-methylquinazolines via sp3 C-H activation under air conditions
Zhao, Dan,Zhu, Min-Xue,Wang, Yue,Shen, Qi,Li, Jian-Xin
, p. 6246 - 6249 (2013/09/23)
An efficient and selective Pd(0)-catalyzed sp3 C-H bond arylation-oxidation of 4-methylquinazolines is reported. The method enables the introduction of arylketone at the benzylic position of 4-methylquinazolines without the use of an additional directing group, and atmospheric oxygen is used as the sole oxidant.
Several approaches to cyanide ion-catalyzed synthesis of 4-aroyl-1-phenyl-1h-pyrazolo[3,4-d]pyrimidines
Miyashita, Akira,Suzuki, Yumiko,Ohta, Kiyono,Iwamoto, Ken-Ichi,Higashino, Takeo
, p. 407 - 414 (2007/10/03)
- 4-Aroyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidines (5) were formed in low yields by reaction of 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (4) with arenecarbaldehydes (3) in the presence of potassium cyanide. Similar reaction of 4-tosyl-1-phenyl-1H-pyra
Synthesis and reactivities of 1,3-dimethyl-2-(α-hydroxy-benzyl)imidazolium and 1,3-dimethyl-2-(α-hydroxybenzyl)benzimidazolium iodides
Miyashita, Akira,Kurachi, Akihito,Matsuoka, Yoshiyuki,Tanabe, Noriko,Suzuki, Yumiko,Iwamoto, Ken-Ichi,Higashino, Takeo
, p. 417 - 426 (2007/10/03)
1,3-Dimethyl-2-(α-hydroxybenzyl)benzimidazolium iodide (3a) was synthesized from 1-methylbenzimidazole (10) through two steps involving lithiation and quaternization. Treatment of 3a with 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (6) afforded 4-benzoyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (15a). 4-Benzoylquinazoline (14a) and 7-benzoyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (16a) were given by reaction of 3a with 4-chloroquinazoline (5) and 7-chloro-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (7). Treatment of 3a with benzaldehyde (9a) gave benzoin (8a). Similar results were obtained in the reactions of 1,3-dimethyl-2-(α-hydroxybenzyl)imidazolium iodide (4a).
Catalytic action of azolium salts. IV. Preparations of 4-aroylquinazolines and 4-aroyl-1H-pyrazolo[3,4-d]pyrimidines by catalytic action of 1,3-dimethylimidazolium iodide
Miyashita,Matsuda,Suzuki,Iwamoto,Higashino
, p. 2017 - 2022 (2007/10/02)
The ability of 1,3-dimethylimidazolium iodide (1) to catalyze the aroylation of the chloroheteroarenes 4-8 with arenecarbaldehydes 3 as sources of the aroyl groups was examined in order to develop a preparative method of aroylheteroarenes. In the presence
