- Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent
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Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.
- Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro
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supporting information
p. 1553 - 1558
(2021/02/26)
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- Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
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We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
- Delost, Michael D.,Njardarson, Jon T.
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supporting information
p. 6121 - 6125
(2021/08/16)
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- Synthetic studies on indolocarbazoles: Total synthesis of staurosporine aglycon
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A synthesis of staurosporine aglycon and its analogs was achieved in a 28-36% overall yield starting from 2-methylindole. The prominent key steps for the synthesis of the indolocarbazole alkaloids involved electrocyclization and nitrene insertion reactions.
- Rajeshwaran, Ganesan Gobi,Mohanakrishnan, Arasambattu K
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supporting information; experimental part
p. 1418 - 1421
(2011/05/04)
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- A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles
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(Chemical Equation Presented) A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline leading to indoles with group at C2-C7. The orthogonal approach of the sequential copper- and palladium-mediated synthesis of 1,2-diarylindoles exploited the wide availability of diverse organoboron reagents.
- Fang, Yuan-Qing,Lautens, Mark
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p. 538 - 549
(2008/09/17)
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- PYRROLOPYRIDINE-2-CARBOXYLIC ACID AMIDES
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Compounds represented by Formula (I) or pharmaceutically acceptable salts thereof, are useful in the prophylactic or therapeutic treatment of diabetes, hyperglycemia, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis or tissue ischemia e.g. myocardial ischemia, and as cardioprotectants.
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Page/Page column 31
(2008/06/13)
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- Substituted 3-imidazo[1,2-a]pyridin-3-yl-4-(1,2,3,4-tetrahydro-[1,4] diazepino-[6,7,1-hi]indol-7-yl)pyrrole-2,5-diones as highly selective and potent inhibitors of glycogen synthase kinase-3
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Glycogen synthase kinase-3 (GSK3) is involved in signaling from the insulin receptor. Inhibitors of GSK3 are expected to effect lowering of plasma glucose similar to insulin, making GSK3 an attractive target for the treatment of type 2 diabetes. Herein we report the discovery of a series of potent and selective GSK3 inhibitors. Compounds 7-12 show oral activity in an in vivo model of type II diabetes, and 9 and 12 have desirable PK properties.
- Engler, Thomas A.,Henry, James R.,Malhotra, Sushant,Cunningham, Brian,Furness, Kelly,Brozinick, Joseph,Burkholder, Timothy P.,Clay, Michael P.,Clayton, Joshua,Diefenbacher, Clive,Hawkins, Eric,Iversen, Philip W.,Li, Yihong,Lindstrom, Terry D.,Marquart, Angela L.,McLean, Johnathan,Mendel, David,Misener, Elizabeth,Briere, Daniel,O'Toole, John C.,Porter, Warren J.,Queener, Steven,Reel, Jon K.,Owens, Rebecca A.,Brier, Richard A.,Eessalu, Thomas E.,Wagner, Jill R.,Campbell, Robert M.,Vaughn, Renee
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p. 3934 - 3937
(2007/10/03)
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- PURINE DERIVATIVES AS KINASE INHIBITORS
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The present invention provides kinase inhibitors of Formula I.
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Page/Page column 65
(2008/06/13)
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- Preparation of Nitrobenzaldehydes and Nitrophenyl Ketones by Electrophilic Amination of Nitrobenzyl Aryl Sulfones
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Nitrobenzyl aryl sulfones 1a-g react with 3,3-pentamethylene-oxaziridine (2) with incorporation of an NH group into the benzylic position, followed by cleavage to nitrobenzaldehydes 4a-d and nitrophenyl ketones 4e-g, respectively.
- Wulf, Jens-Peter,Sienkiewicz, Krzysztof,Makosza, Mieczyslaw,Schmitz, Ernst
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p. 537 - 538
(2007/10/02)
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- Process for the preparation of optionally substituted fluoro-nitro-benzaldehydes
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Optionally substituted fluoro-nitro-benzaldehydes are prepared from optionally substituted halogeno-nitro-benzaldehydes and an alkali metal fluoride in a substantially anhydrous inert aprotic solvent, by heating to 50° to 250° C.
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