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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 6
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Original Articles

A Green Preparation of N-Chloro- and N-Bromosaccharin

Soraia P. L. de Souza Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil
,
Joaquim F. M. da Silva Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil
&
Marcio C. S. de Mattos Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, BrazilCorrespondence[email protected]
Pages 935-939 | Received 03 Apr 2002, Published online: 17 Aug 2006

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Heshmatollah Alinezhad, Sahar Mohseni Tavakkoli & Fatemeh Salehian. (2010) Efficient, Rapid, and Regioselective Bromination of Phenols and Anilines with N-Bromosaccharin Using Tungstophosphoric Acid as a Heterogeneous Recyclable Catalyst. Synthetic Communications 40:21, pages 3226-3232.
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Ardeshir Khazaei, Amin Rostami, Zahra Rosta & Ali Alavi. (2009) N,N′-Dibromo-N,N′–1,2-ethanediylbis(benzene sulfonamide) as an Efficient Catalyst for Acetylation and Formylation of Alcohols Under Mild Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 185:1, pages 181-186.
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Articles from other publishers (29)

Vitor S.C. de Andrade & Marcio C.S. de Mattos. (2023) Oxidative Chlorination: A Sustainable Alternative for the Preparation of Chloroarenes. Current Green Chemistry 10:2, pages 143-159.
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Shunya Hayashi, Kiyosei Takasu & Hiroshi Takikawa. (2023) Sequential Bromination/Dearomatization Reactions of 2-Methoxyphenols en route to Bromo-Substituted ortho-Quinonemonoacetals. Synlett.
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Nilton S. Camilo, Hugo Santos, Lucas A. Zeoly, Fábio S. Fernandes, Manoel T. RodriguesJr.Jr., Thiago S. Silva, Samia R. Lima, José Cláudio Serafim, Aline S. B. de Oliveira, Arthur G. Carpanez, Giovanni W. Amarante & Fernando Coelho. (2022) An Improved Protocol for the Morita‐Baylis‐Hillman Reaction Allows Unprecedented Broad Synthetic Scope. European Journal of Organic Chemistry 2022:9.
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Kamalpreet Kaur & Suman Srivastava. (2020) Artificial sugar saccharin and its derivatives: role as a catalyst. RSC Advances 10:60, pages 36571-36608.
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Nan Kang & Zhanguo Chen. (2018) Base-catalyzed Formation of Enamines from β,β-Dicyanostyrene Derivatives with N-Bromosaccharin. Chemical Research in Chinese Universities 34:5, pages 751-757.
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Bartosz Marciniak, Justyna Walkowiak-Kulikowska & Henryk Koroniak. (2017) On the halofluorination reactions of olefins as selective, and an efficient methodology for the introduction of fluorine into organic molecules. Journal of Fluorine Chemistry 203, pages 47-61.
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Hiroshi Takikawa, Shogo Sato, Ryota Seki & Keisuke Suzuki. (2017) Oxidative Ring Opening of Benzocyclobutenone Oximes: Novel Access to Stable Nitrile Oxides. Chemistry Letters 46:7, pages 998-1000.
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Wagner A.V. da Silva, Daniele C. Rodrigues, Ramon G. de Oliveira, Rhuan K.S. Mendes, Tayná R. Olegário, Juliana C. Rocha, Tatjana S.L. Keesen, Claudio G. Lima-Junior & Mário L.A.A. Vasconcellos. (2016) Synthesis and activity of novel homodimers of Morita–Baylis–Hillman adducts against Leishmania donovani: A twin drug approach. Bioorganic & Medicinal Chemistry Letters 26:18, pages 4523-4526.
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Leonardo S. de Almeida, Pierre M. Esteves & Marcio C.S. de Mattos. (2015) Tribromoisocyanuric acid as a green reagent for benzylic bromination of alkylarenes. Tetrahedron Letters 56:49, pages 6843-6845.
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Ghasem Aghapour, Ali Kazemi Moghaddam & Samaneh Nadali. (2014) Selective Silylation of Alcohols, Phenols and Oximes Using N ‐Chlorosaccharin as an Efficient Catalyst under Mild and Solvent‐Free Conditions . Journal of the Chinese Chemical Society 62:2, pages 197-203.
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Thirumal Yempala, Vijay Darshan Davalgar, Gaddamanugu Gayatri, Prabhakar Sripadi & Srinivas Kantevari. (2015) Insights into the Morita–Baylis–Hillman reaction of isomeric dibenzofuran carbaldehydes: a theoretical and mass spectral study. RSC Advances 5:120, pages 99133-99142.
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Bo Ram Kim, Eun Jung Kim, Gi Hyeon Sung, Jeum-Jong Kim, Dong-Soo Shin, Sang-Gyeong Lee & Yong-Jin Yoon. (2013) One-Pot, Regioselective Consecutive Multihalogenation of 2,2′-Bithiophene. European Journal of Organic Chemistry 2013:14, pages 2788-2791.
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Youngsoon Kim. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Edilson B.A. Filho, Ingrid A. Moraes, Karen C. Weber, Gerd B. Rocha & Mário L.A.A. Vasconcellos. (2012) DFT/PCM, QTAIM, 1H NMR conformational studies and QSAR modeling of thirty-two anti-Leishmania amazonensis Morita–Baylis–Hillman Adducts. Journal of Molecular Structure 1022, pages 72-80.
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Heshmatollah Alinezhad & Shahrouz Fallahi. (2012) An efficient method for the oxathioacetalization of carbonyl compounds using N-bromosaccharin as a catalyst. Chinese Chemical Letters 23:8, pages 927-929.
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Fábio P.L. Silva, Priscilla A.C. de Assis, Claudio G.L. Junior, Natália G. de Andrade, Saraghina M.D. da Cunha, Márcia R. Oliveira & Mário L.A.A. Vasconcellos. (2011) Synthesis, evaluation against Leishmania amazonensis and cytotoxicity assays in macrophages of sixteen new congeners Morita–Baylis–Hillman adducts. European Journal of Medicinal Chemistry 46:9, pages 4295-4301.
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Ticiano P. Barbosa, Suervy C.O. Sousa, Francianne M. Amorim, Yara K.S. Rodrigues, Priscilla A.C. de Assis, John P.A. Caldas, Márcia R. Oliveira & Mário L.A.A. Vasconcellos. (2011) Design, synthesis and antileishmanial in vitro activity of new series of chalcones-like compounds: A molecular hybridization approach. Bioorganic & Medicinal Chemistry 19:14, pages 4250-4256.
Crossref
Heshmatollah Alinezhad, Mahmood Tajbakhsh & Shahram Shahriari Tehrani. (2011) Selective Monobromination of 1,3-Diones with N-Bromosaccharin/Mg(ClO 4 ) 2 System in Solution and under Solvent-Free Conditions . Bulletin of the Korean Chemical Society 32:5, pages 1543-1546.
Crossref
Cláudio G.L. Junior, Priscila A.C. de Assis, Fábio P.L. Silva, Suervy C.O. Sousa, Natália G. de Andrade, Ticiano P. Barbosa, Patrícia L.N. Nerís, Luiz V.G. Segundo, Ítalo C. Anjos, Gabriel A.U. Carvalho, Gerd B. Rocha, Márcia R. Oliveira & Mário L.A.A. Vasconcellos. (2010) Efficient synthesis of 16 aromatic Morita–Baylis–Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi. Bioorganic Chemistry 38:6, pages 279-284.
Crossref
Jana M. Sandes, Andrezza R. Borges, Cláudio G.L. Junior, Fábio P.L. Silva, Gabriel A.U. Carvalho, Gerd B. Rocha, Mário L.A.A. Vasconcellos & Regina C.B.Q. Figueiredo. (2010) 3-Hydroxy-2-methylene-3-(4-nitrophenylpropanenitrile): A new highly active compound against epimastigote and trypomastigote form of Trypanosoma cruzi. Bioorganic Chemistry 38:5, pages 190-195.
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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.
Crossref
Darko Dolenc & Barbara Modec. (2009) EDA Complexes of N-halosaccharins with N- and O-donor ligands. New Journal of Chemistry 33:11, pages 2344.
Crossref
Rodrigo O.M.A. de Souza, Vera L.P. Pereira, Pierre M. Esteves & Mario L.A. A. Vasconcellos. (2008) The Morita–Baylis–Hillman reaction in aqueous–organic solvent system. Tetrahedron Letters 49:41, pages 5902-5905.
Crossref
Habib Firouzabadi, Nasser Iranpoor & Farzaneh Ebrahimzadeh. (2006) Facile conversion of alcohols into their bromides and iodides by N-bromo and N-iodosaccharins/triphenylphosphine under neutral conditions. Tetrahedron Letters 47:11, pages 1771-1775.
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Mário LAA Vasconcellos, Tania MS Silva, Celso A Camara, Rodrigo M Martins, Kelly M Lacerda, Horacimone M Lopes, Vera LP Pereira, Rodrigo OMA de Souza & Lívia TC Crespo. (2006) Baylis–Hillman adducts with molluscicidal activity againstBiomphalaria glabrata. Pest Management Science 62:3, pages 288-292.
Crossref
M.A. Wilson. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 295 356 .
R.O.M.A. de Souza & M.L.A.A. Vasconcellos. (2004) Intrinsic catalytic activity of tertiary amines: a mechanistic proposal to the unexpected temperature effect in Baylis–Hillman reaction. Catalysis Communications 5:1, pages 21-24.
Crossref
Soraia P. L. de Souza, Joaquim F. M. da Silva & Marcio C. S. de Mattos. (2003) A Green Preparation of N‐Chloro‐ and N‐Bromosaccharin.. ChemInform 34:31.
Crossref
Soraia P.L. de Souza, Joaquim Fernando M. da Silva & Marcio C.S. de Mattos. (2003) SiO2 MEDIATED REACTION OF ISATIN WITH N-HALOSACCHARINS: A REGIOSPECIFIC PREPARATION OF 5-HALOISATINS. Heterocyclic Communications 9:1.
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