A one-pot three-component synthesis of novel α-sulfamidophosphonates under ultrasound irradiation and catalyst-free conditions

An efficient and convenient one-pot synthesis of novel α-sulfamidophosphonates is described via a three-component reaction. This reaction was carried out through a three component condensation reaction of sulfonamide, an aromatic aldehyde and triethylphosphite under conventional/ultrasonic techniques, catalyst-free and solvent-free conditions. This methodology was established with many advantages, including mild reaction conditions, short reaction times, good yields, simple work-up procedures, and environmental friendliness.

[1]  M. Berredjem,et al.  One-pot synthesis of novel oxazaphosphinanes under ultrasound irradiation and solvent-free conditions , 2015, Monatshefte für Chemie - Chemical Monthly.

[2]  N. Dupont,et al.  Synthesis and antibacterial activity of sulfonamides. SAR and DFT studies , 2014 .

[3]  M. Berredjem,et al.  A simple, rapid, and efficient N-Boc protection of amines under ultrasound irradiation and catalyst-free conditions , 2014, Monatshefte für Chemie - Chemical Monthly.

[4]  C. Barbey,et al.  Synthesis and structural study of new substituted chiral sulfamoyl oxazolidin-2-ones , 2012 .

[5]  Wenxia Gao,et al.  Tandem base-free synthesis of β-hydroxy sulphides under ultrasound irradiation , 2012, Journal of Chemical Sciences.

[6]  C. Barbey,et al.  Crystal Structure of 4-Phenyl-piperazine-1-sulfonamide , 2010 .

[7]  Dennis G Hall,et al.  Natural product synthesis using multicomponent reaction strategies. , 2009, Chemical reviews.

[8]  Huile Jin,et al.  An efficient catalyst-free protocol for the synthesis of quinoxaline derivatives under ultrasound irradiation , 2009 .

[9]  G. Clarkson,et al.  Rapid synthesis of 1,3,4,4-tetrasubstituted beta-lactams from methyleneaziridines using a four-component reaction. , 2008, The Journal of organic chemistry.

[10]  T. Müller,et al.  Multi-component syntheses of heterocycles by transition-metal catalysis. , 2007, Chemical Society reviews.

[11]  William A. Lee,et al.  Suppression of HIV-1 protease inhibitor resistance by phosphonate-mediated solvent anchoring. , 2006, Journal of molecular biology.

[12]  Giancarlo Cravotto,et al.  Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. , 2006, Chemical Society reviews.

[13]  Alexander Dömling,et al.  Recent developments in isocyanide based multicomponent reactions in applied chemistry. , 2006, Chemical reviews.

[14]  C. Moody,et al.  Discovery and structure-activity relationships of novel sulfonamides as potent PTP1B inhibitors. , 2005, Bioorganic & medicinal chemistry letters.

[15]  Jieping Zhu,et al.  Multicomponent Reactions: ZHU:MULTICOMPONENT REACTIONS O-BK , 2005 .

[16]  B. Kaboudin,et al.  Silica-Supported Ammonium Hydrogen Carbonate as an Efficient Reagent for One-Pot Synthesis of 1-Aminophosphonates from Aldehydes , 2003 .

[17]  N. Azizi,et al.  Lithium Perchlorate‐Catalyzed Three‐Component Coupling: A Facile and General Method for the Synthesis of α‐Aminophosphonates under Solvent‐Free Conditions , 2003 .

[18]  M. Greef,et al.  Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds , 2003 .

[19]  S. Chandrasekhar,et al.  Three component coupling catalyzed by TaCl5–SiO2: synthesis of α-amino phosphonates , 2001 .

[20]  I. Ugi.  Recent progress in the chemistry of multicomponent reactions , 2001 .

[21]  J. Park,et al.  Lanthanide triflate-catalyzed three component synthesis of alpha-amino phosphonates in ionic liquids. A catalyst reactivity and reusability study. , 2001, Chemical communications.

[22]  I. Ugi,et al.  Multicomponent Reactions with Isocyanides. , 2000, Angewandte Chemie.

[23]  Shuj Kobayashi,et al.  Facile synthesis of α-amino phosphonates in water using a Lewis acid–surfactant-combined catalyst , 2000 .

[24]  B. Ranu,et al.  General Procedure for the Synthesis of α-Amino Phosphonates from Aldehydes and Ketones Using Indium(III) Chloride as a Catalyst , 1999 .

[25]  Michael Almstetter,et al.  Discovery of New Multi Component Reactions with Combinatorial Methods , 1999 .

[26]  S. Laschat,et al.  Carbohydrates as Chiral Templates: Stereoselective Synthesis of (R)- and (S)-α-Aminophosphonic Acid Derivatives , 1992 .

[27]  Paweł Kafarski,et al.  BIOLOGICAL ACTIVITY OF AMINOPHOSPHONIC ACIDS , 1991 .

[28]  J. Wood,et al.  Renin inhibitors. Synthesis of transition-state analogue inhibitors containing phosphorus acid derivatives at the scissile bond. , 1989, Journal of medicinal chemistry.

[29]  E. Logusch,et al.  Synthesis of .alpha.- and .gamma.-alkyl-substituted phosphinothricins: potent new inhibitors of glutamine synthetase , 1988 .

[30]  P. Bartlett,et al.  Phosphorus amino acid analogues as inhibitors of leucine aminopeptidase. , 1987, Journal of medicinal chemistry.

[31]  G. Posner.  Multicomponent one-pot annulations forming 3 to 6 bonds , 1986 .

[32]  C. Hassall,et al.  Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. , 1986, Journal of medicinal chemistry.

[33]  A. Gallo,et al.  BIOLOGICALLY ORIENTED ORGANIC SULFUR CHEMISTRY. 19. SYNTHESIS AND PROPERTIES OF 2-AMINO-5-MERCAPTO-5-METHYLHEXANOIC ACID, A BISHOMOLOG OF PENICILLAMINE. USE OF BORON TRIFLUORIDE ETHERATE FOR CATALYZING MARKOVNIKOV ADDITION OF A THIOL TO AN OLEFIN , 2002 .

[34]  I. Ugi,et al.  Isonitrile, II. Reaktion von Isonitrilen mit Carbonylverbindungen, Aminen und Stickstoffwasserstoffsäure , 1961 .