- Application of copper(II)-mediated radical cross-dehydrogenative coupling to prepare spirocyclic oxindoles and to a formal total synthesis of Satavaptan
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Application of radical cross-dehydrogenative coupling (CDC) procedures to prepare a range of novel spirocyclic oxindoles and to a formal total synthesis of the vasopressin V2 receptor antagonist Satavaptan is reported. The key step involves a c
- Hurst, Timothy E.,Gorman, Ryan,Drouhin, Pauline,Taylor, Richard J.K.
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p. 6485 - 6496
(2018/10/05)
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- Substrate scope in the copper-mediated construction of bis-oxindoles via a double C-H/Ar-H coupling process
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Abstract The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)2·H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method.
- Drouhin, Pauline,Hurst, Timothy E.,Whitwood, Adrian C.,Taylor, Richard J.K.
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supporting information
p. 7124 - 7136
(2015/03/30)
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- Synthesis of potent, substituted carbazoles as selective androgen receptor modulators (SARMs)
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The synthesis and in vitro binding affinity for a novel series of potent androgen receptor modulators is described. One of the more potent compounds (17, RAD35010) was further characterized in vivo where it restored levator ani weight in castrated male ra
- Miller, Chris P.,Bhaket, Pushpal,Muthukaman, Nagarajan,Lyttle, C. Richard,Shomali, Maysoun,Gallacher, Kyla,Slocum, Connie,Hattersley, Gary
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scheme or table
p. 7516 - 7520
(2011/02/16)
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- Reaction of Ph3P(SCN)2 with further orthohydroxy carboxylic acid systems, including substituted β-keto acids: Synthesis of novel 2-thio-1,3-oxazines and their subsequent transformation with amines
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We now report the first reaction of Ph3P(SCN)2 with 4,6-dihydroxy-5- methylisophthalic acid to give 10-methyl-2,8-dithio-1,3-oxazino-1,3-benzoxazine- 4,6-dione. Also, the enol tautomer has been utilized in the reaction of β-keto acids with Ph3P(SCN)2 to give novel 2-thio-1,3-oxazines. Subsequent reaction of the 2-thio-1,3-oxazines with benzylamine resulted in opening of the oxazine ring and gave novel dibenzylamino-enamides, which could be cyclized to thiouracils. The reaction of 2-thio-1,3-oxazines with morpholine at low temperature led to the production of unstable 2-Mercapto-2-morpholino-1,3- oxazines. 2-Mercapto-2-morpholin-4-yl-2,3,5,6,7,8-hexahydro-4H-1,3-benzoxazin-4- one was observed to lose H2S at room temperature to give 2-morpholin-4-yl-5,6,7, 8-tetrahydro-4H-1,3-benzoxazin-4-one, which was subsequently tested and found to exhibit some antiplatelet activity. Copyright Taylor & Francis Group, LLC.
- Pritchard, Kaylene M.,Al-Rawi, Jasim
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experimental part
p. 4076 - 4096
(2009/04/11)
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- The 2-oxocyclopentanecarboxylic acid keto-enol system in aqueous solution: Generation of the enol by hydration of an acylketene
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Flash photolysis of 2-diazocyclohexane-1,3-dione in aqueous solution produced 2-ketocyclopentylideneketene, which hydrated to the enol of 2-oxocyclopentanecarboxylic acid, and the enol then isomerized to the keto form of the acid. This ketene proved to be
- Chiang,Kresge,Nikolaev,Popik
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p. 11183 - 11190
(2007/10/03)
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- Carboxylation of Ketones Using Triethylamine and Magnesium Halides
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Procedures for the carboxylation of ketones with carbon dioxide at atmospheric pressure in the presence of magnesium halides and triethylamine are described.A variety of ketones are converted to the corresponding β-keto acids in satisfactory yields by using magnesium chloride-sodium iodide mixtures in acetonitrile.This carboxylation reaction exhibits little regioselectivity with 2-butanone.
- Tirpak, Robin E.,Olsen, Richard, S.,Rathke, Michael W.
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p. 4877 - 4879
(2007/10/02)
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