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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 8
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Original Articles

The Use of DMAP as Catalyst in the Baylis-Hillman Reaction Between Methyl Acrylate and Aromatic Aldehydes

Rodrigo Octavio Núcleo de Pesquisas de Produtos Naturais–Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Ilha do Fundão, RJ, Brazil
,
M. A. de Souza Núcleo de Pesquisas de Produtos Naturais–Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Ilha do Fundão, RJ, Brazil
&
Mário Luiz A. A. Vasconcellos Núcleo de Pesquisas de Produtos Naturais–Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Ilha do Fundão, RJ, BrazilCorrespondence[email protected]
Pages 1383-1389 | Received 15 Jun 2002, Published online: 15 Aug 2006

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Zeinab Faramarzi & Hamzeh Kiyani. (2023) Steglich’s Base Catalyzed Three-Component Synthesis of Isoxazol-5-Ones. Polycyclic Aromatic Compounds 43:4, pages 3099-3121.
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Maryam Khashi, Abolghasem Davoodnia & Jamshidkhan Chamani. (2014) Dmap-Catalyzed Synthesis of Novel Pyrrolo[2,3-D]Pyrimidine Derivatives Bearing an Aromatic Sulfonamide Moiety. Phosphorus, Sulfur, and Silicon and the Related Elements 189:6, pages 839-848.
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Articles from other publishers (23)

Paulo Ricardo dos Santos Correia, Johnnatan Duarte de Freitas, Lucas André Zeoly, Ricardo Silva Porto & Dimas José da Paz Lima. (2023) Discovery and structure-activity relationship of Morita-Baylis-Hillman adducts as larvicides against dengue mosquito vector, Aedes aegypti (Diptera: Culicidae). Bioorganic & Medicinal Chemistry 90, pages 117315.
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Jannis Ludwig, Julian Helberg, Hendrik Zipse & Rainer Herges. (2020) Azo-dimethylaminopyridine-functionalized Ni(II)-porphyrin as a photoswitchable nucleophilic catalyst. Beilstein Journal of Organic Chemistry 16, pages 2119-2126.
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Mehdi Ghandi, Shahzad Feizi, Farhood Ziaie & Behrouz Notash. (2014) Solvent-dependent Baylis–Hillman reactions for the synthesis of 3-benzyl-3-hydroxyoxindoles and benzo-δ-sultams. Tetrahedron 70:15, pages 2563-2569.
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N.E. Leadbeater. 2014. Comprehensive Organic Synthesis II. Comprehensive Organic Synthesis II 234 286 .
Nicholas E. Leadbeater. 2016. Microwave-assisted Polymer Synthesis. Microwave-assisted Polymer Synthesis 1 44 .
Mehdi Ghandi, Abolfazl Hasani Bozcheloei, Seyed Hadi Nazari & Masoud Sadeghzadeh. (2011) Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences. The Journal of Organic Chemistry 76:24, pages 9975-9982.
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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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Irena Pulko, Jennifer Wall, Peter Krajnc & Neil R. Cameron. (2010) Ultra‐High Surface Area Functional Porous Polymers by Emulsion Templating and Hypercrosslinking: Efficient Nucleophilic Catalyst Supports. Chemistry – A European Journal 16:8, pages 2350-2354.
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Giovanni W. Amarante, Mario Benassi, Humberto M. S. Milagre, Ataualpa A. C. Braga, Feliu Maseras, Marcos N. Eberlin & Fernando Coelho. (2009) Brønsted Acid Catalyzed Morita–Baylis–Hillman Reaction: A New Mechanistic View for Thioureas Revealed by ESI‐MS(/MS) Monitoring and DFT Calculations. Chemistry – A European Journal 15:45, pages 12460-12469.
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A. Davoodnia, M. Bakavoli, M. Soleimany & H. Behmadi. (2008) A new one-pot neat synthesis of 1,2,4-triazol-3-ones through 4-(N,N-dimethylamino) pyridine (DMAP) catalyzed cyclocondensation of ethyl carbazate with aryl nitriles. Chinese Chemical Letters 19:6, pages 685-688.
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Angelika Bruckmann, Anke Krebs & Carsten Bolm. (2008) Organocatalytic reactions: effects of ball milling, microwave and ultrasound irradiation. Green Chemistry 10:11, pages 1131.
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Mahiuddin Baidya, Shinjiro Kobayashi, Frank Brotzel, Uli Schmidhammer, Eberhard Riedle & Herbert Mayr. (2007) DABCO and DMAP—Why Are They Different in Organocatalysis?. Angewandte Chemie International Edition 46:32, pages 6176-6179.
Crossref
Mahiuddin Baidya, Shinjiro Kobayashi, Frank Brotzel, Uli Schmidhammer, Eberhard Riedle & Herbert Mayr. (2007) DABCO oder DMAP – worauf beruht ihr Unterschied in der Organokatalyse?. Angewandte Chemie 119:32, pages 6288-6292.
Crossref
R.O.M.A. de Souza, V.L.P. Pereira, M.F. Muzitano, C.A.B. Falcão, B. Rossi-Bergmann, E.B.A. Filho & M.L.A.A. Vasconcellos. (2007) High selective leishmanicidal activity of 3-hydroxy-2-methylene-3-(4-bromophenyl)propanenitrile and analogous compounds. European Journal of Medicinal Chemistry 42:1, pages 99-102.
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Naseem Ahmed, Hasrat Ali & Johan E. van Lier. (2012) The reaction of porphyrins with α,β-acetylenic ketone/ester (Morita-Baylis-Hillman) promoted by MgI 2 and subsequent Sonogashira coupling reactions . Journal of Porphyrins and Phthalocyanines 10:10, pages 1172-1178.
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Davy R. J. Acke & Christian V. Stevens. (2006) Study of the Baylis−Hillman Reaction in a Microreactor Environment:  First Continuous Production of Baylis−Hillman Adducts. Organic Process Research & Development 10:3, pages 417-422.
Crossref
Mamta Dadwal, Shaikh M. Mobin & Irishi N. N. Namboothiri. (2006) Highly efficient hydrazination of conjugated nitroalkenes via imidazole or DMAP mediated Morita–Baylis–Hillman reaction. Org. Biomol. Chem. 4:13, pages 2525-2528.
Crossref
Mamta Dadwal, Renu Mohan, Dulal Panda, Shaikh M. Mobin & Irishi N. N. Namboothiri. (2006) The Morita–Baylis–Hillman adducts of β-aryl nitroethylenes with other activated alkenes: synthesis and anticancer activity studies. Chem. Commun.:3, pages 338-340.
Crossref
Min Shi & Wen Zhang. (2005) Organocatalysts of tertiary-phosphines and amines catalyzed reactions of α-keto esters with cyclopent-2-enone. Tetrahedron 61:50, pages 11887-11894.
Crossref
Cornelia Faltin, Eimear M. Fleming & Stephen J. Connon. (2004) Acrylamide in the Baylis−Hillman Reaction:  Expanded Reaction Scope and the Unexpected Superiority of DABCO over More Basic Tertiary Amine Catalysts. The Journal of Organic Chemistry 69:19, pages 6496-6499.
Crossref
Namrata Rastogi, Irishi N.N. Namboothiri & Miriam Cojocaru. (2004) α-Hydroxymethylation of conjugated nitroalkenes via the Morita–Baylis–Hillman reaction. Tetrahedron Letters 45:24, pages 4745-4748.
Crossref
Declan J. Maher & Stephen J. Connon. (2004) Acceleration of the DABCO-promoted Baylis–Hillman reaction using a recoverable H-bonding organocatalyst. Tetrahedron Letters 45:6, pages 1301-1305.
Crossref
Rodrigo Octavio, M. A. de Souza & Mario Luiz A. A. Vasconcellos. (2003) The Use of DMAP as Catalyst in the Baylis—Hillman Reaction Between Methyl Acrylate and Aromatic Aldehydes.. ChemInform 34:36.
Crossref

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