- The ninhydrin core as carbonyl source to access 2-(2′-hydroxyaryl)benzimidazoles exploiting the ortho selectivity of ninhydrin-phenol adducts
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Although ninhydrin is an essential analytical tool in biochemical and forensic sciences, for the past several years, it has been employed as efficient building block for diverse organic scaffolds. In the present work, the ortho selectivity of ninhydrin-phenol adducts has been exploited to obtain 2-(2′-hydroxyaryl)benzimidazoles which are well known excited state intramolecular proton transfer (ESIPT) fluorophores. Under acidic condition, 3-(2-hydroxyaroyl)isoindolin-1-one intermediate generated in situ from ninhydrin-phenol adducts was treated with o-phenylenediamine resulting benzimidazole scaffolds via a two-step one pot strategy.
- Das, Suven,Maity, Suvendu,Ghosh, Prasanta,Dutta, Arpita
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p. 2862 - 2872
(2021/08/13)
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- An ESIPT based fluorescent probe for imaging hydrogen sulfide with a large turn-on fluorescence signal
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Through an intramolecular nucleophilic substitution reaction and ESIPT mechanism, we designed and synthesized a fluorescent hydrogen sulfide probe with a large turn on fluorescence signal (400-fold). The new probe exhibits high selectivity, good membrane-permeability and is suitable for the visualization of exogenous and endogenous hydrogen sulfide in living cells.
- Deng, Beibei,Ren, Mingguang,Kong, Xiuqi,Zhou, Kai,Lin, Weiying
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p. 62406 - 62410
(2016/07/14)
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- Construction of a turn-on probe for fast detection of H2S in living cells based on a novel H2S trap group with an electron rich dye
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A turn-on probe (ANR) for fast detection of H2S is constructed based on a 2-(azidomethyl)-4-nitrobenzoate moiety as a trap group. This group is very effective for the design of H2S probes especially with electron rich dyes. The potential biological applications of ANR were proved by employing it for fluorescence imaging of H2S in living cells.
- Yang, Qian,Zhan, Fuxu,Wang, Qiufen,Zhuang, Zhiyuan,Zhang, Guangyou,Zheng, Gengxiu
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p. 106156 - 106160
(2015/12/26)
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- Selective C=O reduction in phthalimide with nickel(0) compounds
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The catalytic reduction of phthalimide was achieved using nickel catalysts. The use of catalytic amounts (20% mol) of [Ni(COD)2] or [(dippe)Ni(μ-H)]2 (1) allowed the monoreduction of phthalimide to yield isoindolinone and benzamide, at 140-180 C and 750 psi of H2. When the N-H moiety of phthalimide was protected with a trimethylsilyl group, both C=O groups were reduced to yield (trimethylsilyl)isoindoline. However, when a methyl moiety was used as the protecting group, the C=O groups and the aromatic ring were reduced, using rather similar reaction conditions, due to the formation of 5 A (average) nickel nanoparticles.
- Arevalo, Alma,Ovando-Segovia, Sebastian,Flores-Alamo, Marcos,Garcia, Juventino J.
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p. 2939 - 2943
(2013/06/27)
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- Reaction of 1-ethoxyisoindole with maleimide and its derivatives
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We have reported1 the possibility of conducting the Diels-Alder [4+2]-cycloaddition reaction with isoindoles that exist predominantly in the isoindoline form, due to the Curtin-Hammet principle. Pursuing our research, we used 1-ethoxyisoindole as the most evident analog of 1-aminoisoindole. This compound is a typical simple isoindole existing chiefly as the isoindoline tautomer. We have studied the reactions of 1-ethoxyisoindoles with maleimide and its derivatives as active dienophiles. In addition, this paper describes the synthesis of a novel compound - tri-(2-methoxycarbonyl)benzylamine.
- Levkov, Igor V.,Cassel, Stephanie,Voitenko, Zoia V.,Palamarchuk, Gennady V.,Shishkin, Oleg V.,Shishkina, Svetlana V.,Lattes, Armand,Rico-Lattes, Isabelle
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experimental part
p. 1671 - 1681
(2012/09/11)
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- Crucial role of selenium in the virucidal activity of benzisoselenazol- 3(2h)-ones and related diselenides
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Various N-substituted benzisoselenazol-3(2H)-ones and their non-seleniumcontaining analogues have been synthesized and tested against selected viruses (HHV-1, EMCV and VSV) to determine the extent to which selenium plays a role in antiviral activity. The data presented here show that the presence of selenium is crucial for the antiviral properties of benzisoselenazol-3(2H)-ones since their isostructural analogues having different groups but lacking selenium either did not show any antiviral activity or their activity was substantially lower. The open-chain analogues of benzisoselenazol- 3(2H)-ones-diselenides also exhibited high antiviral activity while selenides and disulfides were completely inactive towards model viruses.
- Pietka-Ottlik, Magdalena,Potaczek, Piotr,Piasecki, Egbert,Mlochowski, Jacek
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experimental part
p. 8214 - 8228
(2011/03/19)
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- Generation and intramolecular reactivity of acyl radicals from alkynylthiol esters under reducing tin-free conditions
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(Matrix presented) The radical chain reaction of benzenethiol with alkynylthiol esters provides a new, valuable protocol for the tin-free generation of acyl radicals that arise from intramolecular substitution at sulfur by the initial sulfanylvinyl radicals.
- Benati, Luisa,Calestani, Gianluca,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Spagnolo, Piero,Strazzari, Samantha
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p. 1313 - 1316
(2007/10/03)
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- Intramolecular Cyclization of Acyl Radicals onto the Azido Group: A New Radical Approach to Cyclized Lactams
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(Equation Presented) Reagents: i, Bu3SnH/AlBN; ii, (TMS)3SiH/AlBN. Aryl- and alkyl-derived azidoacyl radicals, generated from thiolesters by intramolecular homolytic substitution at the sulfur, can undergo five- and six-membered cyclization onto the azido moiety to give cyclized lactams.
- Benati, Luisa,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Spagnolo, Piero,Strazzari, Samantha,Zanardi, Giuseppe
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p. 3079 - 3081
(2007/10/03)
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- Benzocyclobutadienyl anion: Formation and energetics of an antiaromatic molecule
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Benzocyclobutadienyl diazirine (2) was synthesized and reacted with hydroxide ion in a Fourier transform mass spectrometer to afford the conjugate base of benzocyclobutadiene (1a). Authentication of the ion structure was carried out by a derivatization experiment (i.e., 1a was converted to benzocyclobutenone enolate, which has previously been studied), and its reactivity was explored. Thermochemical data for benzocyclobutadiene (1) were obtained (ΔH°(acid) (1) = 386 ± 3 kcal mol-1, EA(1r) = 1.8 ± 0.1 eV, and C-H BDE (1) = 114 ± 4 kcal mol-1), compared to MP2 and B3LYP calculations, and contrasted to a series of model compounds. Cyclobutadienyl radical appears to be quite different from benzocyclobutadienyl radical (1r) and worth further exploration.
- Broadus, Katherine M.,Kass, Steven R.
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p. 6566 - 6571
(2007/10/03)
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- An efficient synthesis of 2-(((9- fluorenylmethoxycarbonyl)amino)methyl)benzoic acid
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An efficient, two-step synthesis of the title compound 3 in 61% overall yield is presented. The synthesis involves hydrazine removal of the N- phthalimide protecting group of α-phthalimido-o-toluic acid (6), followed by N-Fmoc formation with (9-fluorenylm
- Sun, Jung-Hui,Daneker, Wayne F.
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p. 4525 - 4530
(2007/10/03)
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- Low-valent titanium induced reduction of phthalimides and coupling of corresponding isoindoles
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A new method for the reduction of N-substituted phthalimides to the corresponding hydroxy lactams and the coupling of hydroxy lactams is described. We performed the reactions, which induced by low-valent titanium reagent in the aromatic solvent and in the
- Li, Jing,Chen, Jian,Chen, Hai-Bo,Chen, Wei-Xing
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p. 1281 - 1286
(2007/10/03)
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- Chemoselective debenzylation involving removal of a 2-hydroxy-1- phenylethyl group from nitrogen
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In 2-(2-hydroxy-1-phenylethyl)-1-isoindolinone, selective removal of the 2-hydroxy-1-phenylethyl group is conveniently achieved via a 3-step sequence (mesylation, elimination, hydrolysis) without breaking an endocyclic benzylic nitrogen bond.
- Fains, Olivier,Vernon, John M.
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p. 8265 - 8266
(2007/10/03)
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- Reactions of Benzocyclopropene with Sulfonyl Isocyanates and Nitrones: Cycloadditions through C-C ?-Bond Rupture of Three-Membered Ring
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Alkane- and arenesulfonyl isocyanates were added to benzocyclopropene across the C-C ?-bond of the three-membered ring, giving 2-sulfonyl-1-isoindolinones.The reaction with C,N-diphenylnitrone afforded a similar cyclization product, 3,4-dihydro-3,4-diphen
- Kagabu, Shinzo,Saito, Katsuhiro,Watanabe, Hiroyuki,Takahashi, Kensuke,Wada, Katsuaki
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p. 106 - 110
(2007/10/02)
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- Addition Reaction of Sulfonyl Isocyanates to Benzocyclopropene
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Benzocyclopropene reacted with methane- and n-butanesulfonyl isocyanates at room temperature, and arenesulfonyl isocyanates at 60 deg C to afford the corresponding N-sulfonylphthalimidines.
- Kagabu, Shinzo,Inoue, Tatsuo
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p. 2181 - 2182
(2007/10/02)
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- Iminoisoindoline pigments and processes for the preparation thereof
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Iminoisoindolinone pigments of the formula SPC1 Wherein X represents halogen atoms, Y represents a halogen atom, an alkoxy, cycloalkoxy, aralkoxy, aryloxy, alkylthio or arylthio group, R represents an aromatic radical containing a cyclic bound -CONH group, and Q represents an O-atom or the group =N--R and are useful for coloring plastics and lacquers in yellow shades having excellent fastness properties.
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