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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 13
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Original Articles

Chloromethyl Sulfones from Sulfonyl Chlorides via a One‐Pot Procedure

Schuyler Antane Chemical and Screening Sciences, Wyeth Research, CN 8000, Princeton, New Jersey, 08543‐8000, USACorrespondence[email protected]
,
Ronald Bernotas Chemical and Screening Sciences, Wyeth Research, CN 8000, Princeton, New Jersey, 08543‐8000, USA
,
Yanfang Li Chemical and Screening Sciences, Wyeth Research, CN 8000, Princeton, New Jersey, 08543‐8000, USA
,
Robert McDevitt Chemical and Screening Sciences, Wyeth Research, CN 8000, Princeton, New Jersey, 08543‐8000, USA
&
Yinfa Yan Chemical and Screening Sciences, Wyeth Research, CN 8000, Princeton, New Jersey, 08543‐8000, USA
Pages 2443-2449 | Received 03 Mar 2004, Published online: 10 Jan 2011

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P. Sunitha, K. Shiva Kumar, B. Rama Rao & G. Venkateshwarlu. (2008) Microwave assisted efficient synthesis of β-keto-sulfones in aqueous medium. Green Chemistry Letters and Reviews 1:3, pages 179-183.
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Navath Suryakiran, Thummalapalli Srikanth Reddy & Yenamandra Venkateswarlu. (2007) Iodination of β-keto-sulfones using molecular iodine and hydrogen peroxide in aqueous medium: facile synthesis of α-iodomethyl sulfones. Journal of Sulfur Chemistry 28:5, pages 471-476.
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N. Suryakiran, M. Srinivasulu & Y. Venkateswarlu. (2007) Halogenation of β-keto-sulfones using KX/H2O2 in aqueous medium: Synthesis of α-halo β-keto-sulfones and α-halomethyl sulfones. Journal of Sulfur Chemistry 28:4, pages 345-350.
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Maxime D. Crozet, Vincent Rémusat, Christophe Curti & Patrice Vanelle. (2006) Rapid Synthesis of New 5‐Nitroimidazoles as Potential Antibacterial Drugs via VNS Procedure. Synthetic Communications 36:23, pages 3639-3646.
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Articles from other publishers (25)

Alexandria Uritis, Hannah Phillips, Hunter Phillips & Thomas C. Coombs. (2023) House-Meinwald rearrangement of aryl-substituted epoxysulfones in hexafluoroisopropanol (HFIP). Tetrahedron Letters 128, pages 154716.
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Aparna Tyagi, Neha Taneja, Jabir Khan & Chinmoy Kumar Hazra. (2023) I 2 ‐Catalyzed/Mediated C−S and C−I Bond Formation: Solvent‐ and Metal‐Free Approach for the Synthesis of β ‐Keto Sulfones and Branched Sulfones . Advanced Synthesis & Catalysis 365:8, pages 1247-1254.
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Sarosh Iqbal, Ajmal Khan, Rashid Nazir, Shumaila Kiran, Shahnaz Perveen, Khalid M. Khan & Muhammad I. Choudhary. (2020) Synthesis of β -Ketosulfone Derivatives As New Non-Cytotoxic Urease Inhibitors In Vitro . Medicinal Chemistry 16:2, pages 244-255.
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Xiaocong Zhou, Dufen Hu, Xinyi He, Yuanqiang Li, Youqun Chu & Yuanbin She. (2020) Practical and efficient synthesis of aryl trifluoromethyl sulfones from arylsulfonyl chlorides with Umemoto’s reagent II. Tetrahedron Letters 61:5, pages 151465.
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Madithedu Muneeswara, Nallappan Sundaravelu & Govindasamy Sekar. (2019) NBS-mediated synthesis of β-keto sulfones from benzyl alcohols and sodium arenesulfinates. Tetrahedron 75:25, pages 3479-3484.
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Christopher M. Poteat & Vincent N. G. Lindsay. (2019) Controlled α-mono- and α,α-di-halogenation of alkyl sulfones using reagent–solvent halogen bonding. Chemical Communications 55:20, pages 2912-2915.
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Khaled M. Elattar, Ahmed Fekri, Nesma M. Bayoumy & Ahmed A. Fadda. (2017) Sulfones in heterocyclic synthesis: advances in the chemistry of phenyl sulfonylacetophenone. Research on Chemical Intermediates 43:7, pages 4227-4264.
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Vikas S. Rawat, Perla L. M. Reddy & Bojja Sreedhar. (2014) Chemoselective one-pot synthesis of β-keto sulfones from ketones. RSC Advances 4:10, pages 5165.
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Krzysztof M. Borys, Maciej D. Korzyński & Zbigniew Ochal. (2012) A simple and efficient synthesis of trihalomethyl and dihalonitromethyl aryl sulfones. Tetrahedron Letters 53:48, pages 6606-6610.
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Kevin G. Liu, Albert J. Robichaud, Alexander A. Greenfield, Jennifer R. Lo, Cristina Grosanu, James F. Mattes, Yanxuan Cai, Guo Ming Zhang, Jean Y. Zhang, Dianne M. Kowal, Deborah L. Smith, Li Di, Edward H. Kerns, Lee E. Schechter & Thomas A. Comery. (2011) Identification of 3-sulfonylindazole derivatives as potent and selective 5-HT6 antagonists. Bioorganic & Medicinal Chemistry 19:1, pages 650-662.
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Simon N. Haydar, Heedong Yun, Patrick M. Andrae, James Mattes, Jean Zhang, Angela Kramer, Deborah L. Smith, Christine Huselton, Radka Graf, Suzan Aschmies, Lee E. Schechter, Thomas A. Comery & Albert J. Robichaud. (2010) 5-Cyclic Amine-3-arylsulfonylindazoles as Novel 5-HT 6 Receptor Antagonists . Journal of Medicinal Chemistry 53:6, pages 2521-2527.
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Ronald C. Bernotas & Rebecca J. Dooley. (2010) Efficient syntheses of 1,2,3,4,4a,5-hexahydro-pyrazino[2,1-c][1,4]benzothiazine-6,6-dioxide. Tetrahedron 66:13, pages 2273-2276.
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Ronald C. Bernotas, Schuyler Antane, Rajesh Shenoy, Van-Duc Le, Ping Chen, Boyd L. Harrison, Albert J. Robichaud, Guo Ming Zhang, Deborah Smith & Lee E. Schechter. (2010) 3-(Arylsulfonyl)-1-(azacyclyl)-1H-indoles are 5-HT6 receptor modulators. Bioorganic & Medicinal Chemistry Letters 20:5, pages 1657-1660.
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Hossein Loghmani-Khouzani, Dariush Hajiheidari, Ward T. Robinson & Reza Kia. (2009) 2-(Benzo[ d ]thiazol-2-ylsulfonyl)-1-(4-bromophenyl)ethanone . Acta Crystallographica Section E Structure Reports Online 66:1, pages o209-o209.
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Robert R. Singhaus, Ronald C. Bernotas, Robert Steffan, Edward Matelan, Elaine Quinet, Ponnal Nambi, Irene Feingold, Christine Huselton, Anna Wilhelmsson, Annika Goos-Nilsson & Jay Wrobel. (2010) 3-(3-Aryloxyaryl)imidazo[1,2-a]pyridine sulfones as liver X receptor agonists. Bioorganic & Medicinal Chemistry Letters 20:2, pages 521-525.
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Ronald C. Bernotas, Schuyler A. Antane, Steven E. Lenicek, Simon N. Haydar, Albert J. Robichaud, Boyd L. Harrison, Guo Ming Zhang, Deborah Smith, Joseph Coupet & Lee E. Schechter. (2009) 1-(2-Aminoethyl)-3-(arylsulfonyl)-1H-pyrrolopyridines are 5-HT6 receptor ligands. Bioorganic & Medicinal Chemistry Letters 19:24, pages 6935-6938.
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Maxime D. Crozet, Céline Botta, Monique Gasquet, Christophe Curti, Vincent Rémusat, Sébastien Hutter, Olivier Chapelle, Nadine Azas, Michel De Méo & Patrice Vanelle. (2009) Lowering of 5-nitroimidazole's mutagenicity: Towards optimal antiparasitic pharmacophore. European Journal of Medicinal Chemistry 44:2, pages 653-659.
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Roberta Ragni, Enrico Orselli, Gregg S. Kottas, Omar Hassan Omar, Francesco Babudri, Adriana Pedone, Francesco Naso, Gianluca M. Farinola & Luisa De Cola. (2009) Iridium(III) Complexes with Sulfonyl and Fluorine Substituents: Synthesis, Stereochemistry and Effect of Functionalisation on their Photophysical Properties. Chemistry - A European Journal 15:1, pages 136-148.
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Yue-Mei Zhang, Xiaodong Fan, Shyh-Ming Yang, Robert H. Scannevin, Sharon L. Burke, Kenneth J. Rhodes & Paul F. Jackson. (2008) Syntheses and in vitro evaluation of arylsulfone-based MMP inhibitors with heterocycle-derived zinc-binding groups (ZBGs). Bioorganic & Medicinal Chemistry Letters 18:1, pages 405-408.
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N. Suryakiran, P. Prabhakar, K. Rajesh, V. Suresh & Y. Venkateswarlu. (2007) Synthesis of β-keto-sulfones using ionic liquid [TPA][Pro] as an efficient and reusable reaction medium. Journal of Molecular Catalysis A: Chemical 270:1-2, pages 201-204.
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N. Suryakiran, P. Prabhakar, T. Srikanth Reddy, K. Chinni Mahesh, K. Rajesh & Y. Venkateswarlu. (2007) Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones. Tetrahedron Letters 48:5, pages 877-881.
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N. Suryakiran, T. Srikanth Reddy, V. Suresh, M. Lakshman & Y. Venkateswarlu. (2006) Synthesis of α-iodo β-ketosulfones and α-iodo methylsulfones using iodine monochloride. Tetrahedron Letters 47:26, pages 4319-4323.
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Laure C. Bouchez, Māris Turks, Srinivas Reddy Dubbaka, Freddy Fonquerne, Cotinica Craita, Sylvain Laclef & Pierre Vogel. (2005) Sulfur dioxide mediated one-pot, four-component synthesis of polyfunctional sulfones and sulfonamides, including medium-ring cyclic derivatives. Tetrahedron 61:48, pages 11473-11487.
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Schuyler Antane, Ronald Bernotas, Yanfang Li, Robert McDevitt & Yinfa Yan. (2004) Chloromethyl Sulfones from Sulfonyl Chlorides via a One‐Pot Procedure.. ChemInform 35:47.
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Ronald Bernotas, Steven Lenicek, Schuyler Antane, Guo Ming Zhang, Deborah Smith, Joseph Coupet, Boyd Harrison & Lee E. Schechter. (2004) 1-(2-Aminoethyl)-3-(arylsulfonyl)-1H-indoles as novel 5-HT6 receptor ligands. Bioorganic & Medicinal Chemistry Letters 14:22, pages 5499-5502.
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