260391-75-1Relevant academic research and scientific papers
Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for N-tert-butoxycarbonylation of amines under solvent-free conditions at room temperature
Chankeshwara, Sunay V.,Chakraborti, Asit K.
, p. 1087 - 1091 (2006)
Commercially available copper(II) tetrafluoroborate hydrate was found to be a highly efficient catalyst for chemoselective N-tert-butoxycarbonylation of amines with di-tert-butyl dicarbonate under solvent-free conditions and at room temperature. Various aromatic amines were protected as their N-tert-butyl carbamates in high yields and in short times. No competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation was observed. Chemoselective N-tert-butoxycarbonylation was achieved with substrates bearing OH and SH groups. Chiral α-amino acid esters afforded the corresponding N-t-Boc derivatives in excellent yields.
Direct C?H Phosphonylation of Electron-Rich Arenes and Heteroarenes by Visible-Light Photoredox Catalysis
Shaikh, Rizwan S.,Ghosh, Indrajit,K?nig, Burkhard
supporting information, p. 12120 - 12124 (2017/09/13)
The direct transformation of ubiquitous, but chemically inert C?H bonds into diverse functional groups is an important strategy in organic synthesis that improves the atom economy and faclitates the preparation and modification of complex molecules. In contrast to the wide applications of aryl phosphonates, their synthesis via direct C?H bond phosphonylation is a less explored area. We report here a general, mild, and broadly applicable visible-light photoredox C?H bond phosphonylation method for electron-rich arenes and heteroarenes. The photoredox catalytic protocol utilizes electron-rich arenes and biologically important heteroarenes as substrates, [Ru(bpz)3][PF6]2 as photocatalyst, ammonium persulfate as oxidant, and trialkyl phosphites as the phosphorus source to provide a wide range of aryl phosphonates at ambient temperature under very mild reaction conditions.
An Efficient Coupling of p-Quinone Mono-Imine Ketals and Aryl/Alkyl Thiols: Rapid Synthesis of Biaryl/Aryl–Alkyl Sulfides
Sharma, Arun,Peddinti, Rama Krishna
, p. 2230 - 2237 (2017/05/01)
We report a fast, efficient, and metal-free protocol for the synthesis of unsymmetrical biaryl sulfides and aryl–alkyl sulfides (4-methoxy-2-sulfanyl-phenylcarbamates) under catalytic influence of 2,4-dinitrobenzoic acid. The reaction proceeded in a regioselective anti-Michael addition fashion and all the products were obtained within a very short period of time and in good to excellent yields.
Metal-free synthesis of fluorinated indoles enabled by oxidative dearomatization
Vitaku, Edon,Smith, David T.,Njardarson, Jon T.
supporting information, p. 2243 - 2247 (2016/02/18)
Nitrogen heterocycles are found in a majority of approved small-molecule pharmaceuticals, and the number of approved fluorinated drugs is increasing each decade. Therefore, new approaches for accessing fluorinated nitrogen heterocycles are of great significance. A novel, scalable, and metal-free method for accessing a wide range of fluorinated indoles is described. This oxidative-dearomatization-enabled approach assembles 2-trifluoromethyl NH-indole products from simple commercially available anilines with hexafluoroacetylacetone in the presence of an organic oxidant. The nature of the aniline N-capping group is critical for the success of this new reaction. Furthermore, the indole products contain a 3-trifluoroacetyl group, which can be exploited to access a plethora of useful functional groups.
BICYCLIC COMPOUND
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Paragraph 1155; 1156, (2014/09/03)
The present invention provides a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.
Axially chiral dicarboxylic acid catalyzed activation of quinone imine ketals: Enantioselective arylation of enecarbamates
Hashimoto, Takuya,Nakatsu, Hiroki,Takiguchi, Yuka,Maruoka, Keiji
supporting information, p. 16010 - 16013 (2013/11/19)
The synthetic utility of quinone imine ketals in the context of asymmetric catalysis was disclosed for the first time. By expanding the utility of chiral Bronsted acid catalysis to the electrophilic activation of quinone imine ketals, we succeeded in the development of highly enantioselective arylation of encarbamates to give α-amino-β-aryl ethers wherein quinone imine ketals act as functionalized aromatic ring surrogate. Further transformations of the products were also examined to establish procedures to provide chiral β-aryl amines and α-aryl esters.
BICYCLIC COMPOUND
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Page/Page column 66-67, (2011/11/06)
The present invention provides to a compound having an ACC inhibitory action, which is useful as an agent for the prophylaxis or treatment of obesity, diabetes, hypertension, hyperlipidemia, cardiac failure, diabetic complications, metabolic syndrome, sarcopenia, cancer and the like, and has superior efficacy. The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification.
Indium(III) halides as new and highly efficient catalysts for N-tert-butoxycarbonylation of amines
Chankeshwara, Sunay V.,Chakraborti, Asit K.
, p. 2784 - 2788 (2008/02/05)
Indium(III) bromide and chloride efficiently catalysed the N-tert-butoxycarbonylation of amines with (Boc)2O at room temperature and under solvent-free conditions. Various aromatic, heteroaromatic and aliphatic amines were converted to N-tert-butylcarbamates in excellent yields in short times. Chiral amines, esters of α-amino acids and β-amino alcohols afforded optically pure N-t-Boc derivatives in high yields. The reactions were chemoselective and no competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation were observed. Chemoselective conversion to N-tert-butylcarbamates took place with amino alcohols without any formation of oxazolidinones. Georg Thieme Verlag Stuttgart.
HClO4-SiO2 as a new, highly efficient, inexpensive and reusable catalyst for N-tert-butoxycarbonylation of amines
Chakraborti, Asit K.,Chankeshwara, Sunay V.
, p. 2769 - 2771 (2008/03/28)
Perchloric acid adsorbed on silica-gel (HClO4-SiO2) was found to be a new, highly efficient, inexpensive and reusable catalyst for chemoselective N-tert-butoxycarbonylation of amines at room temperature and under solvent-free conditions. The Royal Society of Chemistry 2006.
Synthesis and protein tyrosine phosphatase inhibitory activity of dephostatin analogs
Watanabe,Takeuchi,Otsuka,Tanaka,Umezawa
, p. 1460 - 1466 (2007/10/03)
We have synthesized derivatives of dephostatin, a protein tyrosine phosphatase (PTPase) inhibitor, to study the structure-activity relationships of this inhibitor. Inactive analogs revealed some insight into structural requirements for PTPase inhibitory activity of dephostatin. Both a nitroso group and phenolic hydroxyl groups were found to be essential for the inhibitory activity. Among the dephostatin derivatives synthesized, one of the regioisomers of dephostatin showed PTPase inhibitory activity equivalent to that of dephostatin, and also had increased stability.
