- Sуnthesis and Study of the Properties of New Hybrid Photochromic Chromenes with Reversible Modulation of Fluorescence
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Abstract: The reaction between phenalenon derivatives containing hydroxy group in peri-position to carbonyl and propynol was studied. A new hybrid compound was synthesized, and its spectral-kinetic properties were measured. This compound has photochromic and fluorescent properties in one time.
- Ait, A. O.,Barachevsky, V. A.,Gorelik, A. M.,Venidiktova, O. V.
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p. 2656 - 2659
(2022/01/22)
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- Preparation method of aryl-containing alkynol compounds
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The invention discloses a preparation method of aryl-containing alkynol compounds, and relates to the technical field of preparation of medical intermediates. The method comprises the following steps: dissolving a proper amount of aromatic ketone compounds in an organic solvent, adding trimethylsilylacetylene, and performingcooling reaction; after the reaction is completed, adding a THF solution of LDA, and carrying out heating reaction after keeping the temperature constant; reducing the temperature after the reaction, adding a sodium hydroxide methanol solution, and stirring for reaction; and after the reaction is completed, making the organic solvent evaporated out, adding ethyl acetate for re-dissolution, and obtaining the aryl-containing alkynol compounds through dilution, drying, evaporation and recrystallization. According to the preparation method, the reaction raw materials are easy to obtain, the cost is low, the reaction process is simple, and the temperature is low, so that the reaction process is high in safety, and the product obtained through the reaction is high in purity; and by-products are few, so that the process of side reaction treatment is reduced, and the environment is protected.
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Paragraph 0059-0090
(2021/10/27)
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- Mechanosynthesis of Odd-Numbered Tetraaryl[n]cumulenes
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A mechanochemical synthesis of one-dimensional carbon allotrope carbyne model compounds, namely tetraaryl[n]cumulenes (n=3, 5) was realized. Central for the mechanosynthesis of the cumulenic carbon nanostructures were the development of a mechanochemical Favorskii alkynylation-type reaction and the implementation of a solvent-free, acid-free reductive elimination with tin(II) chloride by ball milling.
- Ardila-Fierro, Karen J.,Bolm, Carsten,Hernández, José G.
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supporting information
p. 12945 - 12949
(2019/08/01)
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- Synthesis, Characterization, and Reactivity of Cationic Gold Diarylallenylidene Complexes
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Methoxide abstraction from gold acetylide complexes of the form (L)Au[η1-C≡CC(OMe)ArAr′] (L=IPr, P(tBu)2(ortho-biphenyl); Ar/Ar′=C6H4X where X=H, Cl, Me, OMe) with trimethylsilyl trifluoromethanesulfonate (TMSOTf) at ?78 °C resulted in the formation of the corresponding cationic gold diarylallenylidene complexes [(L)Au=C=C=CArAr′]+ OTf? in ≥85±5 % yield according to 1H NMR analysis. 13C NMR and IR spectroscopic analysis of these complexes established the arene-dependent delocalization of positive charge on both the C1 and C3 allenylidene carbon atoms. The diphenylallenylidene complex [(IPr)Au=C=C=CPh2]+ OTf? reacted with heteroatom nucleophiles at the allenylidene C1 and/or C3 carbon atom.
- Kim, Nana,Widenhoefer, Ross A.
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supporting information
p. 4722 - 4726
(2018/03/27)
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- Synthesis and biological evaluation of novel N-substituted nipecotic acid derivatives with an alkyne spacer as GABA uptake inhibitors
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In this study, we present the synthesis and structure–activity relationships (SAR) of novel N-substituted nipecotic acid derivatives closely related to (S)-SNAP-5114 (2) in the pursuit of finding new and potent mGAT4 selective inhibitors. By the use of iminium ion chemistry, a series of new N-substituted nipecotic acid derivatives containing a variety of heterocycles, and an alkyne spacer were synthesized. Biological evaluation of the prepared compounds showed, how the inhibitory potency and subtype selectivity for the murine GABA transporters (mGATs) were influenced by the performed modifications.
- Tóth, Krisztián,H?fner, Georg,Wanner, Klaus T.
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p. 3668 - 3687
(2018/06/19)
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- The photophysical behavior of the photochromic naphthopyran derivative having photo-switching ability
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(Graph Presented) The photophysical behavior of the photochromic naphthopyran derivative 9 with photo-switching ability has been investigated in solution phase as well as in crystalline form. The proposed switching motifs might be a versatile framework in
- Kim, Moon-Hwan,Saleem, Muhammad,Seo, Ji-Su,Choi, Chang-Shik,Lee, Ki Hwan
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p. 1291 - 1297
(2015/02/19)
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- Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s
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A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.
- Sun, Lang,Zhu, Yuanxun,Wang, Jing,Lu, Ping,Wang, Yanguang
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supporting information
p. 242 - 245
(2015/02/19)
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- Facile synthesis of halogenated spiroketals via a tandem iodocyclization
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A strategy for the synthesis of spiroketal compounds through a tandem iodocyclization of 1-(2-ethynylphenyl)-4-hydroxybut-2-yn-1-one derivatives is presented. This reaction could proceed under very mild conditions in a short time and avoid the use of expensive and toxic metal catalysts. Moreover, the resulting halides can be further exploited by subsequent palladium-catalyzed coupling reactions, which act as the important intermediates for building other valuable compounds.
- Wang, Jia,Zhu, Hai-Tao,Li, Ying-Xiu,Wang, Li-Jing,Qiu, Yi-Feng,Qiu, Zi-Hang,Zhong, Mei-Jin,Liu, Xue-Yuan,Liang, Yong-Min
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supporting information
p. 2236 - 2239
(2014/05/06)
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- Synthesis of cyano-substituted diaryltetracenes from tetraaryl[3]cumulenes
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A versatile, two-step synthesis of highly substituted, cyano-functionalized diaryltetracenes has been developed, starting from easily accessible tetraaryl[3]cumulenes. This unprecedented transformation is initiated by [2+2] cycloaddition of tetracyanoethy
- Gawel, Przemyslaw,Dengiz, Cagatay,Finke, Aaron D.,Trapp, Nils,Boudon, Corinne,Gisselbrecht, Jean-Paul,Diederich, Francois
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supporting information
p. 4341 - 4345
(2014/05/06)
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- Design of pH responsive clickable prodrugs applied to histone deacetylase inhibitors: A new strategy for anticancer therapy
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The aim of this study was to develop clickable prodrugs bearing a tunable pH responsive linker designed for acidic pH-mediated release of histone deacetylase inhibitors. HDACi are an important class of molecules belonging to the epigenetic modulators used for innovative cancer strategies. The behavior of these prodrugs was determined by a bioluminescence resonance energy transfer assay in living tumor cells. This work demonstrated that this innovative type of clickable prodrugs entered cancer cells and showed restored anti proliferative properties attributed to the effective release of the HDAC inhibitors. A correlation between kinetic studies, dose responses, and biological activities was obtained, making such clickable prodrugs good candidates for new strategies in epigenetic-oriented anticancer therapies.
- Delatouche, Régis,Denis, Iza,Grinda, Marion,Bahhaj, Fatima El,Baucher, Estelle,Collette, Floraine,Héroguez, Valérie,Grégoire, Marc,Blanquart, Christophe,Bertrand, Philippe
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p. 862 - 872
(2014/01/06)
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- Synthesis of electronically modified ru-based neutral 16 VE allenylidene olefin metathesis precatalysts
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Electronic modifications within Ru-based olefin metathesis precatalysts have provided a number of new complexes with significant differences in reactivity profiles. So far, this aspect has not been studied for neutral 16 VE allenylidenes. The first synthe
- Lichtenheldt, Martin,Kress, Steffen,Blechert, Siegfried
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experimental part
p. 5177 - 5186
(2012/10/07)
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- Novel triazolyl derivatives for acidic release of amines
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Triazolyl derivatives of amines were prepared using click chemistry and evaluated as releasing systems in mildly acidic environments. Triazolylcarbamates and alkylamines were obtained, depending on the reactivity of the propargylic intermediates used for the Huisgen cycloaddition. A fast hydrolysis of some derivatives in mildly acidic conditions was achieved. The relative rates were correlated to a proposed mechanism highlighting the complementary role of the triazole ring and carbocation reactivity/stability. Copyright
- Delatouche, Regis,Mondon, Martine,Gil, Adri,Frapper, Gilles,Bachmann, Christian,Bertrand, Philippe
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supporting information; experimental part
p. 401 - 407
(2011/03/18)
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- Triazolyl derivatives for acidic release of alcohols
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New triazolyl-based carbonates and ethers have been investigated as potential alcohol-releasing systems under mild acidic conditions. Triazolyl carbonates could not be prepared because of their apparent instability, whereas ethers were successfully obtained. The rate of hydrolysis of these ethers ramged from a few hours to several days. A theoretical investigation demonstrated that the acidic release of alcohols from triazole derivatives proceeds first by protonation of the triazole ring followed by proton transfer from the triazole ring to the carbonyl group of the carbonates or to the oxygen atom of the ether derivatives. The rate of the decomposition reaction was shown to depend on the length of the N3-H···O hydrogen bond in the intermediate C-NH+/E-NH+ structures and on the stability of the triazole carbocation, which is closely related to the π-donating effect of its R2 and R3 substituents. Copyright
- Mondon, Martine,Delatouche, Regis,Bachmann, Christian,Frapper, Gilles,Len, Christophe,Bertrand, Philippe
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supporting information; experimental part
p. 2111 - 2119
(2011/05/16)
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- Modulation of spectrokinetic properties of o-quinonoid reactive intermediates by electronic factors: Time-resolved laser flash and steady-state photolysis investigations of photochromic 6- and 7-arylchromenes
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A ready synthetic accessibility of a series of 6- and 7-arylchromenes via Pd0-catalyzed Suzuki coupling protocol has permitted a comprehensive investigation of the thermal decay behavior of a broad set of photogenerated o-quinonoid reactive intermediates. It is shown that substantial mesomeric effect between the benzopyran nucleus and the aryl ring at C6 or C7 position of the former renders significant absorption beyond 350 nm such that they are readily photoactivated to yield colored o-quinonoid intermediates. The absorption spectra of the latter are found to be strongly influenced by the substituents on C2-, C6- and C7-aryl rings; indeed the colored absorptions can be conveniently tuned by appropriate choice of substituents. The thermal decay (bleaching phenomenon), which is important from the point of view of their application in ophthalmic lenses, was investigated in each case by μs-ms as well as real-time absorption spec-troscopy. By careful experimentation, we have extracted the decay rate constants for Z,E and E,E o-quinonoid isomers of all 6- and 7-arylchromenes in an attempt to establish a correlation between the electronic attributes with their thermokinetic behavior. From a combined analysis of μs-ms (laser flash) and real-time kinetic data, it is shown that the colored o-quinonoid intermediates decay faster when the C2-aryl and C6-/C7-aryl rings contain electron-donating and electron-accepting groups, respectively. In the same vein, the decay was found to occur slowly for the reversed scenario, while intermediate decay rates are observed when both substituents are electron-donating. Thus, any substituent on the C2-aryl ring that contributes mesomerically to the development of charge on the quinonoid oxygen, and any substituent on the C6-/C7-aryl ring that exerts -I effect appear to expedite thermal decay. Furthermore, evidence is obtained for the first time from μs time-resolved laser-flash spectroscopy for the formation and characterization of the trans,cis (E,Z) o-quinonoid isomer, which has heretofore eluded spectral characterization in the photochromic phenomena of pyrans.
- Moorthy, Jarugu Narasimha,Koner, Apurba L.,Samanta, Subhas,Roy, Ankur,Nau, Werner M.
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supporting information; experimental part
p. 4289 - 4300
(2009/12/07)
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- NOVEL SUBSTITUTED NAPHTHOPYRANS
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Described are novel reversible photochromic 2H-naphtho[1,2-b]pyran compounds, examples of which are compounds having certain substituents at the number 5 carbon atom of the naphtho-portion of the naphthopyran and at the 2-position of the pyran ring. Certain substituents may also be present at the number 6, 7, 8, 9 or 10 carbon atoms of the naphtho portion of the naphthopyran. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.
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Page/Page column 13
(2010/11/08)
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- Observations on the synthesis of photochromic naphthopyrans
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1-Naphthol reacts with 1,1-diarylprop-2-yn-1-ols 5a,b, under alumina catalysis, by two pathways to give the photochromic naphtho[1,2-b]pyrans 6a,b, together with the propenylidenenaphthalenones 7a,b, representatives of a new class of merocyanine dyes. With 2-methyl-1-naphthol, formation of the photochrome is suppressed; the only products are merocyanines 7c,d. The cyclocondensation of 2-naphthol with 5a,b proceeds much more efficiently, to give the naphtho[2,1-b]pyrans 14a,b. Pyran formation is not suppressed from either 1-bromo- or 1-(4 -methoxyphenyl)-2-naphthol; reaction with 5a,b merely results in expulsion of the C-1 substituent. An alternative pathway supervenes in the reaction of 1-methyl-2-naphthol with 5a to give the benz[e]indanone 17, the constitution of which was determined by X-ray crystallography. Reaction of the 1,3,3-triarylpropynols 19a,b with 1-naphthol affords the naphthopyrans 20 together with merocyanines 21, whilst the isomeric pyrans 23 are efficiently produced from 2-naphthol. The configuration of merocyanines 7a and 21a was unequivocally established by X-ray crystallography. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Gabbutt, Christopher D.,Heron, B. Mark,Instone, Alicia C.,Thomas, David A.,Partington, Steven M.,Hursthouse, Michael B.,Gelbrich, Thomas
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p. 1220 - 1230
(2007/10/03)
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- Benzopyrans
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Described are novel reversible photochromic benzopyran compounds, examples of which are compounds substituted at the 2 position of the pyran ring and have fused at the benzo portion of the benzopyran a substituted or unsubstituted heterocyclic ring such as a benzothieno or benzofurano group. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel benzopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.
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