3724-43-4Relevant academic research and scientific papers
Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses
Liang, Fengying,Eda, Kazuo,Okazoe, Takashi,Wada, Akihiro,Mori, Nobuaki,Konishi, Katsuhiko,Tsuda, Akihiko
, p. 6504 - 6517 (2021/05/06)
The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.
acyl triazole derivative and its manufacturing method
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Paragraph 0053, (2017/04/03)
PROBLEM TO BE SOLVED: To provide a novel acyl triazole derivative that can be synthesized at low cost by a convenient method, has a comparable reactivity to an acid chloride with an amine compound and an alcohol compound, and can be safely handled, and a method of manufacturing the same; the acyl triazole derivative that is useful as a reactant applied to polymerization reaction to be continued; and a monomer comprising the same.SOLUTION: An acyl triazole derivative is shown by formula (1). In the formula, A denotes a substituted arylene group, a 1,3-phenylene group, a bisarylene group, a polycyclic arylene group, an alkylene group or an aralkylene group.
PROCESS FOR PREPARING SOLID (CHLORINE METHYLENE) DIMETHYL AMMONIUM CHLORIDE
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Paragraph 0021-0023, (2016/12/22)
Solid (chloro methylene) dimethyl ammonium chloride of in manufacturing method, said method, and phthalic anhydride raw material is first acyl with Neel thio chloride and method for chlorinating side is performed on the stacking section for stacking o-reel chloride, again chloride reel-o N, reacts with N-dimethylformamide (chloro methylene) dimethyl ammonium chloride and, and phthalic anhydride is obtained, N of increased amount of generated, and phthalic anhydride, dissolving the-dimethylformamide N, solid-liquid through separation of solid (chloro methylene) dimethyl ammonium chloride to obtain. the method number 1-step reaction through the interrupt input is an input from the data input sulfur dioxide, high vacuum under conditions protruded from sulfur dioxide and does not require the removal of, , moderating reaction conditions, to implemented very easily in.
Syntheses of 4-substituted 2-(trichloromethyl)quinazolines under mild conditions by benzyne [4+2] cycloaddition
Lechuga-Eduardo, Harim,Olivo, Horacio F.,Romero-Ortega, Moises
, p. 5910 - 5913 (2015/03/30)
An experimentally simple and convenient synthesis of 4-susbstituted 2-(trichloromethyl)quinazolines by cycloaddition of benzyne with 2-(trichloromethyl)-1,3-diazabutadienes was developed. The 2-(trichloromethyl)-1,3-diazabutadienes (R1 = H and Me) were prepared from trichloroacetamidine and the appropriate N,N-dimethylamide dimethyl acetal or from trichloroacetamidine and a Vilsmeier-Haack reagent containing an aryl group.
New preparation method for Vilsmeier reagent and related imidoyl chlorides
Kimura, Yoshikazu,Matsuura, Daisuke,Hanawa, Takeshi,Kobayashi, Yukimoto
experimental part, p. 1116 - 1118 (2012/03/26)
An environmentally benign and inexpensive preparation method is described of some imidoyl chlorides, including the Vilsmeier reagent (VR), by using phthaloyl dichloride. Synthetic applications were demonstrated using the isolated VR or VR prepared in situ for the transformation of acids to acid chlorides, alcohols to chlorides, and the formylation of dimethylaminobenzene.
Stereoselective control in the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents: Experimental investigation and theoretical rationalization
Qi, Hengzhen,Li, Xinyao,Xu, Jiaxi
supporting information; experimental part, p. 2702 - 2714 (2011/05/19)
The stereoselectivity of the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents was investigated experimentally by determination of the product stereochemistry and theoretically via DFT calculations. The results indicate that imines preferentially attack the less sterically hindered exo-side of the ketenes to generate zwitterionic intermediates. Subsequently, for cyclic imines, the intermediates undergo a conrotatory ring closure directly to produce β-lactams, while for linear imines, the imine moiety of the intermediates isomerizes to more stable intermediates, which further undergo a conrotatory ring closure to afford trans-β-lactams. The steric hindrance and the isomerization, rather than the torquoelectronic effect, play crucial roles in controlling the stereoselectivity in the practical Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents, although the unaccessible borylketene with a powerful electron acceptor group controls the stereoselectivity torquoelectronically, in theory.
New Vilsmeier reaction for facile synthesis of 4-phenyl-2,4- dihydrochromeno[4,3-c]pyrazoles with Bis(trichloromethyl) carbonate/DMF
Chen, Zhiwei,Yang, Yanyan,Su, Weike
experimental part, p. 661 - 664 (2011/03/18)
An efficient method for the synthesis of 4-phenyl-2,4-dihydrochromeno[4,3- c]pyrazoles via the cyclisation reaction of the easily available flavanone-4-arylhydrazones with Vilsmeier reagent (Bis(trichloromethyl) carbonate/DMF) has been developed.
Diastereoselective total synthesis of 8-epigrosheimin
Yang, Haishen,Qiao, Xiaoxiao,Li, Fangyi,Ma, Hui,Xie, Longguan,Xu, Xiaohua
supporting information; experimental part, p. 1110 - 1112 (2009/05/27)
The first diastereoselective total synthesis of 8-epigrosheimin was accomplished relying entirely on substrate-controlled methods. 8-Epigrosheimin, isolated as an amoebicidal and antibiotic compound from Crepis virens, is a multi-chiral-centered guaianolide with a cis-hydroazulene and a trans-annulated γ-butyrolactone ring. Our approach featured that the γ-butyrolactone unit was formed firstly before the construction of the cycloheptane ring system. The key steps of the synthesis involved (1) a stereoselective Mukaiyama aldol addition; (2) an oxidative γ-lactonization; and (3) an intramolecular aldehyde-ene cyclization.
Highly planar amphiphilic porphyrins
Oda, Masafumi,Ishizuka, Tomoya,Arai, Shigeo,Takano, Atsushi,Jiang, Donglin
supporting information; experimental part, p. 7137 - 7140 (2010/02/27)
A first synthesis of an asymmetric and amphiphilic β-substituted porphyrin is reported. The porphyrin can be integrated into various types of nanostructures with the amphiphilic characters in hydrophilic solvents. The one-dimensional integration may induc
Generation of Phosphorus Oxychloride as by-Product from Phosphorus Pentachloride and DMF and its Use for Chlorination Reaction by Converting Into Vilsmeier-Haack Reagent
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Page/Page column title page; 2-3; Fig.1, (2009/05/28)
A process is described wherein after formation of first crop of Vilsmeier-Haack reagent by reacting Phosphorus Pentachloride with N,N-dimethylformamide to form a first crop of Vilsmeier reagent as insoluble crystals, a by-product of this reaction, the Phosphorus Oxy-Chloride, reacts with N,N-dimethylformamide to give a second crop of Vilsmeier reagent. This second crop of Vilsmeier reagent is soluble in DMF. This process makes it possible to double the yield of chlorinated substrate, such as sucrose-6-acetate or sucrose-6-benzoate, from the same quantity of Phosphorus Pentachloride.
