A microwave-assisted new synthesis of sulfonylidene–sulfonamide via reactions of N-sulfonylketenimine and sodium arylsulfinates

References

• Henry RJ. The mode of action of sulfonamides. Bacteriol Rev. 1943;7:175–262.
   PubMedGoogle Scholar
• Madigan M, Martinko J, Stahl D, et al. Brock biology microorganisms. 13th ed. San Francisco (CA): Benjamin Cummings; 2012. p. 797.
   Google Scholar
• Drew J. Drug discovery: a historical perspective. Science. 2000;287:1960–1964.
   PubMed Web of Science ®Google Scholar
• Casini A, Scozzafava A, Mastrolorenzo A, et al. Sulfonamides and sulfonylated derivatives as anticancer agents. Curr Cancer DrugTargets. 2002;2:55–75.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors. Curr Med Chem Immunol Endoc Metab Agents. 2001;1:61–97.
   Google Scholar
• Boyd AE. Sulfonylurea receptors, ion channels, and fruit flies. Diabetes. 1988;37:847–850.
   PubMed Web of Science ®Google Scholar
• Maren TH. Relations between structure and biological activity of sulfonamides. Annu Rev Pharmacol Toxicol. 1976;16:309–327.
   PubMed Web of Science ®Google Scholar
• Thornber CW. Isosterism and molecular modification in drug design. Chem Soc Rev. 1979;8:563–580.
   Web of Science ®Google Scholar
• Supuran CT, Scozzafava A, Mastrolorenzo A. Bacterial proteases: current therapeutic use and future prospects for the development of new antibiotics. Exp Opin Ther Patents. 2001;11:221–259.
   Web of Science ®Google Scholar
• Prilezhaeva EN. Sulfones and sulfoxides in the total synthesis of biologically active natural compounds. Russ Chem Rev. 2000;69:367–408.
   Google Scholar
• Simpkins NS. Sulfones in organic synthesis. Oxford: Pergamon Press; 1993.
   Google Scholar
• Michaely WJ, Krattz GW. US Patent 4780127, 1988; Chem Abstr. 1989;111:129017.
   Google Scholar
• Sakya SM, Hou XJ, Minich ML, et al. 5-Heteroatom substituted pyrazoles as canine COX-2 inhibitors. Part III: molecular modeling studies on binding contribution of 1-(5-methylsulfonyl)pyrid-2-yl and 4-nitrile. Bioorg Med Chem Lett. 2007;17:1067–1072.
   PubMed Web of Science ®Google Scholar
• Fuchs DL, Braish TF. Multiply convergent syntheses via conjugate-addition reactions to cycloalkenyl sulfones. Chem Rev. 1986;86:903–917.
   Web of Science ®Google Scholar
• Taylor RJK, Casy G. The Ramberg–Bäcklund reaction. Org React. 2003;62:359–475.
   Google Scholar
• Blakemore PR. The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds. J Chem Soc Perkin Tranc. 2002;1:2563–2585.
   Google Scholar
• Grossert JS. In the chemistry of sulphones and sulphoxides. Patai S, Rapoport Z, Stirling CJM, editors. Chichester: Wiley; 1988.
   Google Scholar
• Simpkins NS. Sulphones in organic synthesis. Oxford: Pergamon Press; 1993.
   Google Scholar
• Julia M, Righini A, Verpeaux JN. Couplage des sulfones allyliques avec des reactifs de grignard en presence de cuivre synthese d’olefines. Tetrahedron. 1979;20:2393–2396.
   Google Scholar
• Lu P, Wang Y. The thriving chemistry of ketenimines. Chem Soc Rev. 2012;41:5687–5707.
   PubMed Web of Science ®Google Scholar
• Hein JE, Fokin VV. Copper-catalyzed azide–alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides. Chem Soc Rev. 2010;39:1302–1315.
   PubMed Web of Science ®Google Scholar
• Lu P, Wang Y. Strategies for heterocyclic synthesis via cascade reactions based on ketenimines. Synlett. 2010; 00:165–173.
   Web of Science ®Google Scholar
• Rostovtsev VV, Green LG, Fokin VV, et al. Stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem Int Ed. 2002;114:2708–2711.
   Google Scholar
• Husmann R, Na YS, Bolm C, et al. Copper-catalyzed one-pot synthesis of α-functionalized imidates. Chem Commun. 2010;46:5494–5496.
   PubMed Web of Science ®Google Scholar
• Zhou F, Liu X, Zhang N, et al. Copper-catalyzed three-component reaction: solvent-controlled regioselective synthesis of 4-amino- and 6-amino-2-iminopyridines. Org Lett. 2013;15:5786–5789.
   PubMed Web of Science ®Google Scholar
• Yavari I, Nematpour M. Copper-catalyzed tandem synthesis of tetrasubstituted pyrimidines from alkynes, sulfonyl azides, trichloroacetonitrile, and tetramethylguanidine. Synlett. 2013;24:165–168.
   Web of Science ®Google Scholar
• Yavari I, Nematpour M, Yavari S, et al. Copper-catalyzed one-pot synthesis of tetrasubstituted pyrazoles from sulfonyl azides, terminal alkynes, and hydrazonoyl chlorides. Tetrahedron Lett. 2012;53:1889–1890.
   Web of Science ®Google Scholar
• Yavari I, Nematpour M. Tandem synthesis of highly functionalized pyrazole derivatives from terminal alkynes, sulfonyl azides, diethyl azadicarboxylate, and sodium arylsulfinates. Mol Divers. 2012;16:651–657.
   PubMed Web of Science ®Google Scholar
• Yavari I, Nematpour M, Ghazanfarpour-Darjani M. One-pot synthesis of 2,6-diamino-4-sulfonamidopyrimidines from sulfonyl azides, terminal alkynes and cyanoguanidine. Tetrahedron Lett. 2012;53:942–943.
   Web of Science ®Google Scholar
• Yavari I, Nematpour M. Tandem synthesis of highly functionalized N-phosphorylated sulfonamido-pyrazolone derivatives. Tetrahedron Lett. 2013;54:5061–5063.
   Web of Science ®Google Scholar