1611-83-2Relevant articles and documents
Solid polymer substrates and coated fibers containing 2,4,6-trinitrobenzene motifs as smart labels for the visual detection of biogenic amine vapors
Pablos, Jesús L.,Vallejos, Saúl,Mu?oz, Asunci?n,Rojo, María J.,Serna, Felipe,García, Félix C.,García, José M.
, p. 8733 - 8736 (2015)
Attempts to polymerize trinitrobenzene derivatives (TNB) have been fruitless so far. Accordingly, polymers containing TNB have not been exploited in spite of their envisaged potential applications. Here, we describe two ways for preparing polymers with TNB moieties thus overcoming the previously reported polymerization impairments. We also report on the exploitation of the materials, both obtained as tractable transparent films and coated fibers, as smart labels for the visual detection of amine vapors. More precisely, amines in the atmosphere surrounding the sensory materials diffuse into them reacting with the TNB motifs forming highly colored Meisenheimer complexes, giving rise to development of color and to the naked eye sensing phenomenon. This is the case of highly volatile amines, such as trimethylamine, produced in food spoilage, specifically in the deterioration of fish or meat, for which the color development of the smart labels can be used as a visual test for food freshness.
In vivo and in vitro effects of methacrylanilides and acetylcarboxanilide on alkaline phosphatase activity of Echinococcus multilocularis metacestodes
Audin, P,Sarciron, ME,Paris, J,Petavy, AF
, p. 285 - 289 (1992)
In our search for effective chemotherapy of alveolar hydatid disease we are investigating key enzymes of Echinococcus multilocularis metacestodes.Isatin (2,3-indolinedione) is well known as an inhibitor of alkaline phosphatase activity, and has been previously investigated.Acetylcarboxanilide, an "open drug" of isatin and 2 methacrylanilides were evaluated for their ability to inhibit alkaline phosphatase activity of Echinococcus multilocularis metacestodes in vivo.These "open drugs" are more efficient than isatin, and para-chloromethacrylanilide exhibits a strongselectivity for the parasite enzyme and is also effective in vitro.The results obtained with para-chloromethacrylanilide are promising.Echinococcus multilocularis / alkaline phosphatase / synthetic inhibitors /anilides
Efficient synthesis of aromatic sec-amides from esters: Synthetic utility of bislithium amides
Ooi, Takashi,Tayama, Eiji,Yamada, Masao,Maruoka, Keiji
, p. 729 - 730 (1999)
Convenient, efficient preparation of aromatic sec-amides from esters has been accomplished using dilithium amides which are easily prepared by treatment of aromatic amines with 2 equiv of BuLi in THF. This new method allows a facile formation of amide bond even with sterically hindered esters.
Electrochemical reduction of fluoroalkyl sulfones for radical fluoroalkylation of alkenes
Deng, Ling,Hu, Jinbo,Ni, Chuanfa,Zhou, Xin
supporting information, p. 8750 - 8753 (2021/09/08)
Radical fluoroalkylation of alkenes has been developed by electrochemical reduction of fluoroalkyl sulfones. A series of electron-deficient alkenes readily undergo hydrofluoroalkylation in good to excellent yields. This chemistry represents the first example of electrochemical generation of fluoroalkyl radicals from sulfones, which are used for practical radical fluoroalkylation of organic compounds.
A benzene-bridged divanadium complex-early transition metal catalyst for alkene alkylarylation with PhI(O2CR)2viadecarboxylation
Zhang, Lei,Zhou, Hongfei,Bai, Shaokun,Li, Shaodan
supporting information, p. 3201 - 3206 (2021/03/16)
The synthesis, structure and catalytic activity of a benzene-bridged divanadium complex were comprehensively studied. The reduction of (Nacnac)VCl2(1) (Nacnac = (2,6-iPr2C6H3NCMe)2HC) supported by β-diketiminate with potassium graphite (KC8) by employing benzene as the solvent allows access to the benzene-bridged inverted-sandwich divanadium complex (μ-η6:η6-C6H6)[V(Nacnac)]2(2a), which can catalyze alkene alkylarylation with hypervalent iodine(iii) reagents (HIRs)viadecarboxylation to generate regioselectively diverse indolinones. Furthermore, the mild nature of this reaction was amenable to a wide range of functionalities on alkenes and HIRs. Mechanistic studies revealed a relay sequence of decarboxylative radical alkylation/radical arylation/oxidative re-aromatization.
Bromo Radical-Mediated Photoredox Aldehyde Decarbonylation towards Transition-Metal-Free Hydroalkylation of Acrylamides at Room Temperature
Deng, Guo-Jun,Huang, Huawen,Sun, Zhaozhao,Wang, Qiaolin
supporting information, (2021/12/03)
Herein, we report a visible-light-mediated hydroalkylation reaction of alkenes using easily available aldehydes as alkyl sources via bromo radical-promoted photoredox decarbonylation. This protocol provides an alternative entry to C(sp3)?C(sp3) bond formation and features considerable advantages including mild and clean reaction conditions, obviation for transition-metal catalyst, and good functional group compatibility.
Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals
Das, Sanju,De Sarkar, Suman,Mandal, Tanumoy
supporting information, (2021/12/10)
A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.
Chemistry of Tertiary Carbon Center in the Formation of Congested C?O Ether Bonds
Hirata, Goki,Takeuchi, Kentarou,Shimoharai, Yusuke,Sumimoto, Michinori,Kaizawa, Hazuki,Nokami, Toshiki,Koike, Takashi,Abe, Manabu,Shirakawa, Eiji,Nishikata, Takashi
supporting information, p. 4329 - 4334 (2020/12/23)
Nucleophilic substitutions, including SN1 and SN2, are classical and reliable reactions, but a serious drawback is their intolerance for both bulky nucleophiles and chiral tertiary alkyl electrophiles for the synthesis of a chiral quaternary carbon center. An SRN1 reaction via a radical species is another conventional method used to carry out substitution reactions of bulky nucleophiles and alkyl halides, but chiral tertiary alkyl electrophiles cannot be used. Therefore, a stereospecific nucleophilic substitution reaction using chiral tertiary alkyl electrophiles and bulky nucleophiles has not yet been well studied. In this paper, we describe the reaction of tertiary alkyl alcohols and non-chiral or chiral α-bromocarboxamides as a tertiary alkyl source for the formation of congested ether compounds possessing two different tertiary alkyl groups on the oxygen atom with stereoretention.
Silver-Promoted Fluorination Reactions of α-Bromoamides
Mizuta, Satoshi,Kitamura, Kanami,Kitagawa, Ayako,Yamaguchi, Tomoko,Ishikawa, Takeshi
, p. 5930 - 5935 (2021/02/01)
Silver-promoted C?F bond formation in α-bromoamides by using AgF under mild conditions is reported. This simple method enables access to tertiary, secondary, and primary alkyl fluorides involving biomolecular scaffolds. This transformation is applicable to primary and secondary amides and shows broad functional-group tolerance. Kinetics experiments revealed that the reaction rate increased in the order of 3°>2°>1° α-carbon atom. In addition, it was found that the acidic amide proton plays an important role in accelerating the reaction. Mechanistic studies suggested generation of an aziridinone intermediate that undergoes subsequent nucleophilic addition to form the C?F bond with stereospecificity (i.e., retention of configuration). The synthesis of sterically hindered alcohols and ethers by using AgI is also demonstrated. Examples of reactions of α-bromoamides with O nucleophiles are presented.
Polysubstituted tryptamine benzamide compound and preparation method and application thereof
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Paragraph 0038, (2020/05/30)
The invention discloses a polysubstituted tryptamine benzamide compound and a preparation method and application thereof. The compound is characterized in that the compound is a polysubstituted tryptamine benzamide compound with a structural formula shown as a formula I or a pharmaceutically acceptable salt, ester or solvate of the polysubstituted tryptamine benzamide compound with the structuralformula shown as the formula I. The preparation method comprises the following steps: (1) carrying out amide synthesis reaction on a compound shown in a formula II and a compound shown in a formula III to obtain a compound shown in a formula IV; and (2) reacting the compound as shown in the formula IV with V to carry out Michael addition reaction so as to obtain a compound as shown in the formulaI. The polysubstituted tryptamine benzamide compound and a preparation method and application thereof have the advantages that tumor growth can be effectively inhibited, so that growth stagnation, differentiation or apoptosis of tumor cells is induced, and the effect of inhibiting tumor cell proliferation is achieved.
