- Synthesis of chiral 3-substituted phthalides via rhodium(I)-catalyzed crossed alkyne cyclotrimerisation
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3-Substituted phthalides were synthesized for the first time by crossed alkyne cyclotrimerisations with Wilkinson's catalyst. Esterification of propiolic acids with chiral propargylic alcohols by either the DCC/DMAP or the Mitsunobu method allows the synt
- Witulski, Bernhard,Zimmermann, Axel
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- Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation
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The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.
- Jia, Bing,Yang, Yunhui,Jin, Xiqing,Mao, Guoliang,Wang, Congyang
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p. 6259 - 6263
(2019/09/06)
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- Catalytic asymmetric synthesis of 3-aryl phthalides enabled by arylation-lactonization of 2-formylbenzoates
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The catalytic asymmetric synthesis of 3-aryl phthalides is reported through a sequential asymmetric arylation-lactonization reaction. The reaction is enabled by a boron-zinc exchange to generate reactive arylating agents, which react with 2-formylbenzoates in the presence of a chiral amino naphthol ligand. The enantiodetermining step is the arylation of the aldehyde, which then undergoes a lactonization event to yield the corresponding phthalides in good yields and enantioselectivities.
- Carlos, Andressa M. M.,Stieler, Rafael,Lüdtke, Diogo S.
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supporting information
p. 283 - 289
(2019/01/10)
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- Reductive Heterocyclization of 2-Cyanobenzophenones by the Action of NaBH4. New Efficient Synthesis of 3-Arylphthalides
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The reduction of 2-cyclopropylcarbonyl-, 2-(thiophen-2-yl)carbonyl-, and 2-arylcarbonylbenzonitriles with sodium tetrahydridoborate afforded 3-cyclopropyl-, 3-(2-thiophen-2-yl)-, and 3-arylphthalides, respectively, in high yields. Under analogous conditions, 3-cyanobenzophenones were converted to the corresponding 3-cyanobenzhydrols.
- Mochalov,Fedotov,Trofimova,Zefirov
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p. 568 - 572
(2018/06/11)
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- A concise synthesis of 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4-b]pyridin-5(7H)-ones], 3-aryl-, and alkylphthalides
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A synthetically useful protocol has been developed for the preparation of highly functionalized 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4-b]pyridin-5(7H)-ones], 3-aryl-, and alkylphthalides. Reaction of 2-iodobenzoate esters and 2-iodopyridine carboxylate esters with i-PrMgCl·LiCl in the presence of cyclic ketones under standard Barbier reaction conditions affords 3,4-fused spiro[isobenzofuran-3-ones] and spiro[furo[3,4-b]pyridin-5(7H)-ones] in good to excellent yields. Step-wise addition of i-PrMgCl·LiCl to 2-iodobenzoate esters followed by trapping with various aldehydes yields 3-aryl and 3-alkylphthalides; whereas, under similar conditions access to 3-aryl and 3-alylazaphthalides is also possible. Extension of this methodology toward the preparation of 3-n-butylphthalide and chrycolide, a natural product isolated from the leaves and stems of Chrysanthemum coronarium, is also described.
- Kuethe, Jeffrey T.,Maloney, Kevin M.
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p. 5248 - 5258
(2013/06/27)
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- Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones
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The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm).
- Gerbino, Dario C.,Augner, Daniel,Slavov, Nikolay,Schmalz, Hans-Guenther
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supporting information; experimental part
p. 2338 - 2341
(2012/06/16)
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- Synthesis of biarylketones and phthalides from organoboronic acids and aldehydes catalyzed by cobalt complexes
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A cobalt-catalyzed addition of aryl- and alkenylboronic acids to aldehydes and phthalaldehyde to give the corresponding biarylketones and 3-aryl phthalides in good to excellent yields in one pot is described.
- Karthikeyan, Jaganathan,Parthasarathy, Kanniyappan,Cheng, Chien-Hong
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supporting information; experimental part
p. 10461 - 10463
(2011/11/06)
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- Cascade synthesis of racemic 3-arylphthalides
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Use of the modified reagent system of NaBH4-Amberlyst-15 (H +) for the reduction of o-aroylbenzoates 1a-f followed by simple trituration in aqueous HCl, results in the formation of 3-arylphthalide 3a-f in very short reaction time.
- Patil,Karnik
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p. 710 - 712
(2008/09/18)
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- Efficient synthesis of isobenzofuran-1(3H)-ones (Phthalides) and selected biological evaluations
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The studies presented here deal with the convenient and efficient one-step conversion of o-alkylbenzoic acids into their corresponding isobenzofuran-1 (3H)-ones (phthalides) using NaBrO3/NaHSO3 in a two-phase system. A range of o-alkylbenzoic acids was used with the object of getting a variety of phthalide derivatives as multipurpose biologically active compounds. Seventeen phthalides have been synthesized and tested for cytotoxicity, antibacterial and antifungal activities. Some of these compounds showed promising cytotoxic effects against Artemia salina. Compounds 4j-4p were highly active against Gram-negative and Gram-positive bacteria among all tested compounds. In the fungicidal assay, the compounds showed a broad spectrum of activity against six fungi. All compounds were characterized via elemental analysis, UV, IR, mass and-NMR spectroscopy. ECV · Editio Cantor Verlag.
- Bayer, Ernst,Hayat, Safdar,Atta-Ur-Rahman,Choudhary, M. Iqbal,Khan, Khalid Mohammed,Shah, Syed Tasadaque Ali,Imran-Ul-Haq,Anwar, M. Usman,Voelter, Wolfgang
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p. 588 - 597
(2007/10/03)
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- An alternative method for the synthesis of γ-lactones by using cesium fluoride-celite/acetonitrile combination
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A variety of 2-(1-bromoalkyl) benzoic acids 4 undergo intramolecular nucleophilic substitution reaction when treated with a CsF-Celite as solid base in acetonitrile under reflux condition to give the corresponding cyclized phthalides in moderate to very good yield. These 2-(1-bromoalkyl) benzoic acids 4 are formed by the α-bromination of 2-alkylbenzoic acids 3 using N-bromosuccinimide and a catalytic amount of α,α′ -azoisobutyronitrile in carbon tetrachloride under reflux.
- Khan, Khalid Mohammed,Hayat, Safdar,Zia-Ullah,Atta-ur-Rahman,Iqbal-Choudhary,Maharvi, Ghulam Murtaza,Bayert, Ernst
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p. 3435 - 3453
(2007/10/03)
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