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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 10
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Original Articles

REGIOSELECTIVE NITRATION OF 1-ACYL-4-METHOXYINDOLINES LEADS TO EFFICIENT SYNTHESIS OF A PHOTOLABILE l-GLUTAMATE PRECURSOR

George Papageorgiou National Institute for Medical Research, The Ridgeway, Mill Hill, London, NW7 1AA, UK
&
John E. T. Corrie National Institute for Medical Research, The Ridgeway, Mill Hill, London, NW7 1AA, UKCorrespondence[email protected]
Pages 1571-1577 | Received 17 Apr 2001, Published online: 12 Dec 2006

Citations (18)

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Xiaowei Wang, Yu Gao, Yang Xu, Li Li, Zhili Zhang & Junyi Liu. (2009) Efficient Preparation of Photolabile Agent MNI-glu by Regioselective Nitration of 4-Methoxyindoline Derivative. Synthetic Communications 39:22, pages 4030-4038.
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Articles from other publishers (17)

George Papageorgiou & John E. T. Corrie. (2022) Synthesis and Photolytic Assessment of Nitroindolinyl-Caged Calcium Ion Chelators. Molecules 27:9, pages 2645.
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Shan Tang, Jing-Yuan Cheng & Ji-Shen Zheng. (2015) An Fmoc-compatible method for synthesis of peptides containing photocaged aspartic acid or glutamic acid. Tetrahedron Letters 56:31, pages 4582-4585.
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A. Vasanits-Zsigrai, O. Majercsik, G. Tóth, A. Csámpai, Cs. Haveland-Lukács, D. Pálfi, Z. Szadai, B. Rózsa & I. Molnár-Perl. (2015) Quantitation of various indolinyl caged glutamates as their o-phthalaldehyde derivatives by high performance liquid chromatography coupled with tandem spectroscopic detections: Derivatization, stoichiometry and stability studies. Journal of Chromatography A 1394, pages 81-88.
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Francisco Palma-Cerda, Céline Auger, Duncan J. Crawford, Andrew C.C. Hodgson, Stephen J. Reynolds, Justin K. Cowell, Karl A.D. Swift, Ondrej Cais, Ladislav Vyklicky, John E.T. Corrie & David Ogden. (2012) New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups. Neuropharmacology 63:4, pages 624-634.
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Matthew C. Davis & Thomas J. Groshens. (2012) Nitration of tert-butyloxycarbonylated aniline and 1,3,5-triaminobenzene by acetyl nitrate. Tetrahedron Letters 53:32, pages 4154-4155.
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Axel Griesbeck, Michael Oelgemöller & Francesco GhettiChristian Bochet & Aurélien Blanc. 2012. CRC Handbook of Organic Photochemistry and Photobiology, Third Edition - Two Volume Set. CRC Handbook of Organic Photochemistry and Photobiology, Third Edition - Two Volume Set 73 93 .
George Papageorgiou, Marco Beato & David Ogden. (2011) Synthesis and photolytic evaluation of a nitroindoline-caged glycine with a side chain of high negative charge for use in neuroscience. Tetrahedron 67:29, pages 5228-5234.
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George Papageorgiou & John E.T. Corrie. (2007) Synthesis of an anionically substituted nitroindoline-caged GABA reagent that has reduced affinity for GABA receptors. Tetrahedron 63:39, pages 9668-9676.
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Günter Mayer & Alexander Heckel. (2006) Biologically Active Molecules with a “Light Switch”. Angewandte Chemie International Edition 45:30, pages 4900-4921.
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Günter Mayer & Alexander Heckel. (2006) Biologisch aktive Moleküle mit “Lichtschalter”. Angewandte Chemie 118:30, pages 5020-5042.
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George Papageorgiou, David Ogden, Geoff Kelly & John E. T. Corrie. (2005) Synthetic and photochemical studies of substituted 1-acyl-7-nitroindolines. Photochemical & Photobiological Sciences 4:11, pages 887-896.
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George Papageorgiou, Andreas Barth & John E. T. Corrie. (2005) Flash photolytic release of alcohols from photolabile carbamates or carbonates is rate-limited by decarboxylation of the photoproduct. Photochemical & Photobiological Sciences 4:2, pages 216-220.
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George Papageorgiou & John E.T. Corrie. (2005) Optimised synthesis and photochemistry of antenna-sensitised 1-acyl-7-nitroindolines. Tetrahedron 61:3, pages 609-616.
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George Papageorgiou, David Ogden & John E. T. Corrie. (2004) An Antenna-Sensitized Nitroindoline Precursor to Enable Photorelease of l -Glutamate in High Concentrations . The Journal of Organic Chemistry 69:21, pages 7228-7233.
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George Papageorgiou, Matthew Lukeman, Peter Wan & John E. T. Corrie. (2004) An antenna triplet sensitiser for 1-acyl-7-nitroindolines improves the efficiency of carboxylic acid photorelease. Photochemical & Photobiological Sciences 3:4, pages 366-373.
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George Papageorgiou & John E. T. Corrie. (2010) Regioselective Nitration of 1‐Acyl‐4‐methoxyindolines Leads to Efficient Synthesis of a Photolabile L‐Glutamate Precursor.. ChemInform 33:40, pages 196-196.
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James Morrison, Peter Wan, John E. T. Corrie & George Papageorgiou. (2002) Mechanisms of photorelease of carboxylic acids from 1-acyl-7-nitroindolines in solutions of varying water content. Photochemical & Photobiological Sciences 1:12, pages 960.
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