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Synthesis 2010(15): 2599-2603
DOI: 10.1055/s-0029-1218819
DOI: 10.1055/s-0029-1218819
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkHighly Efficient One-Pot Synthesis of N-Acylsulfonamides Using Cyanuric Chloride at Room Temperature
Weitere Informationen
Received
5 March 2010
Publikationsdatum:
17. Juni 2010 (online)
Publikationsverlauf
Publikationsdatum:
17. Juni 2010 (online)
Abstract
A highly efficient and very mild one-pot synthesis of N-acylsulfonamides is described using cyanuric chloride. In this synthesis, structurally diverse carboxylic acids and sulfonamides are reacted in the presence of cyanuric chloride, triethylamine, and alumina in anhydrous acetonitrile at room temperature to afford various N-acylsulfonamides in excellent yields.
Key words
one-pot - N-acylsulfonamide - sulfonamide - carboxylic acid - cyanuric chloride
- 1a
Blotny G. Tetrahedron 2006, 62: 9507Reference Ris Wihthout Link - 1b
Giacomelli G.Porcheddu A.De Luca L. Curr. Org. Chem. 2004, 8: 1497Reference Ris Wihthout Link - 2a
Olah GA.Narang SC.Fung AP.Gupta BGB. Synthesis 1980, 657Reference Ris Wihthout Link - 2b
Maetz P.Rodriguez M. Tetrahedron Lett. 1997, 38: 4221Reference Ris Wihthout Link - 3
Olah GA.Fung AP.Gupta BGB.Narang SC. Synthesis 1980, 221 - 4a
Rolfe A.Probst DA.Volp KA.Omar I.Flynn DL.Hanson PR. J. Org. Chem. 2008, 73: 8785Reference Ris Wihthout Link - 4b
Venkataraman K.Wagle DR. Tetrahedron Lett. 1980, 21: 1893Reference Ris Wihthout Link - 5
Venkataraman K.Vagle DR. Tetrahedron Lett. 1980, 21: 1893 - 6
Kangani CO.Day BW. Org. Lett. 2008, 10: 2645 - 7a
Venkataraman K.Wagle DR. Tetrahedron Lett. 1979, 20: 3037Reference Ris Wihthout Link - 7b
Bandgar BP.Pandit SS. Tetrahedron Lett. 2002, 43: 3413Reference Ris Wihthout Link - 7c
Kaminski ZJ.Paneth P.Rudzinski J. J. Org. Chem. 1998, 63: 4248Reference Ris Wihthout Link - 7d
Rayle HL.Fellmeth L. Org. Process Res. Dev. 1999, 3: 172Reference Ris Wihthout Link - 7e
Khalafi-Nezhad A.Zare A.Parhami A.Soltani Rad MN.Nejabat GR. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182: 657Reference Ris Wihthout Link - 7f
De Luca L.Giacomelli G.Porcheddu A. Org. Lett. 2001, 3: 1519Reference Ris Wihthout Link - 7g
De Luca L.Giacomelli G.Taddi M. J. Org. Chem. 2001, 66: 2534Reference Ris Wihthout Link - 7h
Forbs DC.Barret EJ.Lewis DL.Smith MC. Tetrahedron Lett. 2000, 41: 9943Reference Ris Wihthout Link - 7i
Falorni M.Porcheddu A.Taddei M. Tetrahedron Lett. 1999, 40: 4395Reference Ris Wihthout Link - 8
Blotny G. Tetrahedron Lett. 2003, 44: 1499 - 9
Porcheddu A.Giacomelli G.Salaris M. J. Org. Chem. 2005, 70: 2361 - 10a
De Luca L.Giacomelli G.Porcheddu A. J. Org. Chem. 2002, 67: 6272Reference Ris Wihthout Link - 10b
Furuya Y.Ishihara K.Yamamoto H. J. Am. Chem. Soc. 2005, 127: 11240Reference Ris Wihthout Link - 11
Das B.Venkateswarlu K.Krishnaiah M. Helv. Chim. Acta 2007, 90: 149 - 12a
De Luca L.Giacomelli G.Procheddo A. Org. Lett. 2002, 4: 552Reference Ris Wihthout Link - 12b
De Luca L.Giacomelli G.Procheddo A. J. Org. Chem. 2002, 67: 5152Reference Ris Wihthout Link - 13a
Soltani Rad MN.Khalafi-Nezhad A.Asrari Z.Behrouz S.Amini Z.Behrouz M. Synthesis 2009, 3983Reference Ris Wihthout Link - 13b
De Luca L.Giacomelli G. J. Org. Chem. 2008, 73: 3967Reference Ris Wihthout Link - 14a
Sharma GVM.Reddy JJ.Lakshmi PS.Krishna PR. Tetrahedron Lett. 2004, 45: 7729Reference Ris Wihthout Link - 14b
Sharma GVM.Reddy KL.Lakshmi PS.Krishna PR. Synthesis 2006, 55Reference Ris Wihthout Link - 14c
Bigdeli MA.Heravi MM.Mahdavinia GH. Catal. Commun. 2007, 8: 1595Reference Ris Wihthout Link - 14d
De Luca L.Giacomelli G.Porcheddu A. Org. Lett. 2002, 4: 553Reference Ris Wihthout Link - 14e
Bandgar BP.Joshi NS.Kamble VT. Tetrahedron Lett. 2006, 47: 4775Reference Ris Wihthout Link - 14f
Bigdeli MA.Mahdavinia GH.Jafari S.Hazarkhani H. Catal. Commun. 2007, 8: 2229Reference Ris Wihthout Link - 15
Vogel AI. Practical Organic Chemistry Longmans, Green, and Co.; London: 1954. Chap. 2. p.161-176 - 16
Singh DU.Singh PR.Samant NT. Tetrahedron Lett. 2004, 45: 4805 - 17
Reddy CR.Mahipal B.Yaragorla SR. Tetrahedron Lett. 2007, 48: 7528