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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 10
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Original Articles

Synthesis of Useful Intermediates from the Claisen-Rearrangement of α-Hydroxy Alkyl Acrylate Precursors

Siegfried E. Drewes Department of Chemistry, University of Natal, Pietermaritzburg, 3200, South Africa
,
Neville D. Emslie Department of Chemistry, University of Natal, Pietermaritzburg, 3200, South Africa
,
Nazira Karodia Department of Chemistry, University of Natal, Pietermaritzburg, 3200, South Africa
&
Georgia Loizou Department of Chemistry, University of Natal, Pietermaritzburg, 3200, South Africa
Pages 1437-1443 | Received 14 Feb 1990, Published online: 24 Oct 2006

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D. P. Kamat, S. G. Tilve, V. P. Kamat & J. K. Kirtany. (2015) Syntheses and Biological Activities of Chroman-2-ones. A Review. Organic Preparations and Procedures International 47:1, pages 1-79.
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SiegfriedE. Drewes & MarkB. Rohwer. (1997) 2-Formylimidazole as Substrate in Baylis-Hillman Reactions: Synthesis of a β-Substituted Acrylate. Synthetic Communications 27:3, pages 415-424.
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PaulH. Mason, NevilleD. Emslie & SiegfriedE. Drewes. (1995) A New Route to Substituted Glutaric Acid Derivatives from Allylic Malonates. Synthetic Communications 25:2, pages 183-190.
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C. Navarro, M. Degueil-Castaing, D. Colombani & B. Maillard. (1993) Synthesis of Alkyl 2-(1-t-Butylperoxyalkyl)propenoates and Ethyl 2-t-Butylperoxymethylbut-2-enoate. Synthetic Communications 23:7, pages 1025-1037.
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Articles from other publishers (28)

Anna Nikitjuka, Melita Ozola, Kristaps Krims‐Davis & Raivis Žalubovskis. (2023) Design, Synthesis, and Bioactivity Evaluations of 3‐Methylenechroman‐2‐one Derivatives as Thioredoxin Reductase (TrxR) Inhibitors. ChemMedChem 19:3.
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Prashant Shukla, Ambika Asati, Devkumari Patel, Manorama Singh, Vijai K. Rai & Ankita Rai. (2023) Novel Synergistic Catalysis by Ethylcarbodiimide Hydrochloride Salt and CuI Towards Morita‐Baylis‐Hillman Reaction. ChemistrySelect 8:5.
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Soundararajan Karthikeyan, Radha Krishnan Shobana, Kamarajapurathu Raju Subimol, J Helen Ratna Monica & Ayyanoth Karthik Krishna Kumar. (2020) Azidophosphonium salt-directed chemoselective synthesis of ( E )/( Z )-cinnamyl-1 H -triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts . Beilstein Journal of Organic Chemistry 16, pages 1579-1587.
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Vinicius Sobral Silva, Terezinha Alves Tolentino, Tiago Costa Alves Fontoura Rodrigues, Fernanda Ferrari Martins Santos, Daniel Francisco Scalabrini Machado, Wender Alves Silva, Heibbe Cristhian Benedito de Oliveira & Angelo Henrique Lira Machado. (2019) Unprecedented E -stereoselectivity on the sigmatropic Hurd–Claisen rearrangement of Morita–Baylis–Hillman adducts: a joint experimental–theoretical study . Organic & Biomolecular Chemistry 17:18, pages 4498-4511.
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A. F. M. Fahmy, S. A. Rizk, M. M. Hemdan, A. A. El‐Sayed & A. I. Hassaballah. (2018) Efficient Green Synthesis and Computational Chemical Study of Some Interesting Heterocyclic Derivatives as Insecticidal Agents. Journal of Heterocyclic Chemistry 55:11, pages 2545-2555.
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Sameh A. Rizk, Galal A. Elsayed & Maher A. El-Hashash. (2018) One-pot synthesis, spectroscopic characterization and DFT study of novel 8-azacoumarin derivatives as eco-friendly insecticidal agents. Journal of the Iranian Chemical Society 15:9, pages 2093-2105.
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Fadia Al Haj Hussien, Mohammad Keshe, Khaled Alzobar, Joumaa Merza & Ayman Karam. (2016) Synthesis and Nitration of 7-Hydroxy-4-Methyl Coumarin via Pechmann Condensation Using Eco-Friendly Medias. International Letters of Chemistry, Physics and Astronomy 69, pages 66-73.
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Deevi Basavaiah & Gorre Veeraraghavaiah. (2012) The Baylis–Hillman reaction: a novel concept for creativity in chemistry. Chem. Soc. Rev. 41:1, pages 68-78.
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Tioga J. Martin, Venus G. Vakhshori, Yang S. Tran & Ohyun Kwon. (2011) Phosphine-Catalyzed β′-Umpolung Addition of Nucleophiles to Activated α-Alkyl Allenes. Organic Letters 13:10, pages 2586-2589.
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Min Shi, Feijun Wang, Mei-Xin Zhao & Yin WeiMei-Xin Zhao, Yin Wei & Min Shi. 2011. The Chemistry of the Morita-Baylis-Hillman Reaction. The Chemistry of the Morita-Baylis-Hillman Reaction 209 324 .
Deevi Basavaiah, Bhavanam Sekhara Reddy & Satpal Singh Badsara. (2010) Recent Contributions from the Baylis−Hillman Reaction to Organic Chemistry. Chemical Reviews 110:9, pages 5447-5674.
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Zvi RappoportSergei M. Lukyanov & Alla V. Koblik. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Sebastien Alaux, Mie Kusk, Emanuelle Sagot, Jean Bolte, Anders A. Jensen, Hans Bräuner-Osborne, Thierry Gefflaut & Lennart Bunch. (2005) Chemoenzymatic Synthesis of a Series of 4-Substituted Glutamate Analogues and Pharmacological Characterization at Human Glutamate Transporters Subtypes 1−3. Journal of Medicinal Chemistry 48:25, pages 7980-7992.
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Tomasz Janecki & Tomasz Wąsek. (2004) A novel route to substituted 3-methylidenechroman-2-ones and 3-methylchromen-2-ones. Tetrahedron 60:5, pages 1049-1055.
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Olivier Roy, François Loiseau, Abdelkhalek Riahi, Françoise Hénin & Jacques Muzart. (2003) Access to racemic and enantioenriched 3-methyl-4-chromanones: catalysed asymmetric protonation of corresponding enolic species as the key step. Tetrahedron 59:48, pages 9641-9648.
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Deevi Basavaiah, Anumolu Jaganmohan Rao & Tummanapalli Satyanarayana. (2003) Recent Advances in the Baylis−Hillman Reaction and Applications. Chemical Reviews 103:3, pages 811-892.
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Olivier Roy, Abdelkhalek Riahi, Françoise Hénin & Jacques Muzart. (2000) Synergy or Competition between Palladium-Catalysis and KF/Alumina-Mediation for the Allylic Substitution of the Acetates of Baylis–Hillman Adducts by Phenols. Tetrahedron 56:41, pages 8133-8140.
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Virgil Helaine, Joël Rossi & Jean Bolte. (1999) A new access to alkyl-α-ketoglutaric acids, precursors of glutamic acid analogues by enzymatic transamination. Application to the synthesis of (2S,4R)-4-propyl-glutamic acid. Tetrahedron Letters 40:36, pages 6577-6580.
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Engelbert Ciganek. 2004. Organic Reactions. Organic Reactions 201 350 .
Aleksandr Kasatkin, Takanori Yamazaki & Fumie Sato. (2003) Reactions of β,γ‐ and γ,δ‐Unsaturated Esters with the Reagent Ti(O i Pr) 4 /2 i PrMgCl: Formation of β‐Titanated Esters, β‐Titanated Cyclobutanones, and Acyltitanium Compounds . Angewandte Chemie International Edition in English 35:17, pages 1966-1968.
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Aleksandr Kasatkin, Takanori Yamazaki & Fumie Sato. (2006) Reaktion von β,γ‐ und γ,δ‐ungesättigten Estern mit dem Ti(O i Pr) 4 /2 i PrMgCl‐Reagens: Bildung von β‐titanierten Estern, β‐titanierten Cyclobutanonen oder Acyltitan‐Verbindungen . Angewandte Chemie 108:17, pages 2091-2093.
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Deevi Basavaiah, Polisetti Dharma Rao & Rachakonda Suguna Hyma. (1996) The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction. Tetrahedron 52:24, pages 8001-8062.
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Deevi Basavaiah & Subramanian Pandiaraju. (1995) The Johnson-Claisen rearrangement of 3-hydroxy-2-methylenealkanenitriles: Stereoselective synthesis of functionalized trisubstituted alkenes. Tetrahedron Letters 36:5, pages 757-758.
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Peter Wipf. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 827 873 .
S. E. DREWES, N. D. EMSLIE, N. KARODIA & G. LOIZOU. (2016) ChemInform Abstract: Synthesis of Useful Intermediates from the Claisen Rearrangement of α‐Hydroxy Alkyl Acrylate Precursors.. ChemInform 21:52.
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