Microwave-induced rapid access to aromatic and heteroaromatic sulfonamides under solvent-free conditions without using external base

Synthetic Communications

Volumn 34, Issue 20, 2004, Pages 3807-3819

  Sharma, Ashwani Kumar ^a   Das, Saibal Kumar ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Aromatic; Heteroaromatic; Solvent free; Sulfonamide

Indexed keywords

ANILINE DERIVATIVE; AROMATIC COMPOUND; BASE; HETEROCYCLIC COMPOUND; MESYLIC ACID DERIVATIVE; SILANE DERIVATIVE; SOLVENT; SULFONAMIDE; TETRAMETHYLSILANE; UNCLASSIFIED DRUG;

ARTICLE; HEATING; INFRARED SPECTROSCOPY; MELTING POINT; MICROWAVE IRRADIATION; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 7444225806     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200032530     Document Type: Article

References (26)

1. For review, see: Green, T.W.; Wuts, P.G. Protective Groups in Organic Synthesis, 2nd Ed.; Wiley: New York, 1991; 379-386.
2. (a) Repa, J.J.; Turley, S.D.; Lobaccaro, J.-M.A.; Medina, J.; Li, L.; Lustig, K.; Shan, B.; Heyman, R.A.; Dietschy, J.M.; Mangelsdorf, D.J. Regulation of absorption and ABC1-mediated efflux of cholesterol by RXR heterodimers. Science 2000, 289, 1524-1529;
3. (b) Li, L.; Medina, J.C.; Hasegawa, H.; Liu, J.; Zhu, L.; Shan, B.; Lustig, K. Preparation of bis(trifluoromethyl)hydroxymethylbenzenesulfonamides, -ureas, and -carbamates as liver X receptor modulators. PCT Patent No. WO 00/054759, 2000; Chem. Abstr. 2000, 133, 237693.
4. Lumma, W.C., Jr.; Wohl, R.A.; Davey, D.D.; Argentieri, T.M.; De Vita, R.J.; Gomez, R.P.; Jain, V.K.; Marisca, A.J.; Morgan, T.K., Jr.; Reiser, H.J.; Sullivan, M.E.; Wiggins, J.; Wong, S.S. Rational design of 4-[(methylsulfonyl) amino]benzamides as class III antiarrhythmic agents. J. Med. Chem. 1987, 30, 755-758.
5. Shan, B.; Medina, J.C.; Santha, E.; Frankmoelle, W.P.; Chou, T.-C.; Learned, R.M.; Narbut, M.R.; Stott, D.; Wu, P.; Jaen, J.C.; Rosen, T.; Timmermans, P.B.M.W.M.; Beckmann, H. Selective, covalent modification of β-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors. Proc. Natl. Acad. Sci. USA 1999, 96, 5686-5691.
6. (a) Penning, T.D.; Talley, J.J.; Bertenshaw, S.R.; Carter, J.S.; Collins, P.W.; Docter, S.; Graneto, M.J.; Lee, L.F.; Malecha, J.W.; Miyashiro, J.M.; Rogers, R.S.; Regier, D.J.; Yu, S.S.; Anderson, G.D.; Berton, E.G.; Cogburn, J.N.; Gregory, S.A.; Koboldt, C.M.; Perkins, W.E.; Seibert, K.; Veenhuizen, A.W.; Zhang, Y.Y.; Isakson, P.C. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib). J. Med. Chem. 1997, 40, 1347-1365;
7. (b) Talley, J.J.; Brown, D.L.; Carter, J.S.; Graneto, M.J.; Koboldt, C.M.; Masferrer, J.L.; Perkins, W.E.; Rogers, R.S.; Shaffer, A.F.; Zhang, Y.Y.; Zweifel, B.S.; Seibert, K. 4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, Valdecoxib: A potent and selective inhibitor of COX-2. J. Med. Chem. 2000, 43, 775-777.
8. For review, see: Iqbal, J.; Sanghi, R.; Das, S.K. Endothelin receptor antagonists: An overview of their synthesis and structure-activity relationship. Mini Rev. Med. Chem. 2004, in press.
9. (a) Tokuyama, H.; Sato, M.; Ueda, T.; Fukuyama, T. A practical route to quinolines from anilines. Heterocycles 2001, 54, 105-108;
10. (b) Baxter, N.J.; Rigoreau, L.J.M.; Laws, A.P.; Page, M.I. Reactivity and mechanism in the hydrolysis of β-sultams. J. Am. Chem. Soc. 2000, 122, 3375-3385;
11. (c) Boulos, L.S.; Hennawy, I.T.; Arsanious, M.H.N. Reactions of phosphites with 1,4-benzoquinone monoimines. Liebigs Ann. Chem. 1993, 351-354;
12. (d) Kim, S.Y.; Sung, N.-D.; Choi, J.-K.; Kim, S.S. 1H-benzotriazol-1-yl methanesulfonate: a regioselective N-mesylating reagent. Tetrahedron Lett. 1999, 40, 117-120.
13. (a) Mingos, D.M.P.; Baghurst, D.R. Applications of microwave dielectric heating effects to synthetic problems in chemistry. Chem. Soc. Rev. 1991, 20, 1-47;
14. (b) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis - A review. Tetrahedron 2001, 57, 9225-9283;
15. (c) Perreux, L.; Loupy, A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 2001, 57, 9199-9223.
16. 3-catalyzed Ferrier rearrangement of acetylglycals: synthesis of 2,3-unsaturated C-glycosides. Tetrahedron Lett. 2003, 44, 4507-4509;
17. 3-catalyzed Ferrier rearrangement of acetylglycals: synthesis of 2,3-unsaturated glycopyranosides. Synlett 2003, 1607-1610.
18. (a) Schantl, J.G.; Hebeisen, P.; Karpellus, P. N-(Arenesulfonyl)-N- phenylhydrazones. Synth. Commun. 1989, 19, 39-48;
19. (b) Katritzky, A.R.; Zhang, G.; Wu, J. 1-Phenylsulfonylbenzotriazole: a novel and convenient reagent for the preparation of benzenesulfonamides and aryl benzenesulfonates. Synth. Commun. 1994, 24, 205-216;
20. (c) Kondo, K.; Sekimoto, E.; Nakao, J.; Murakami, Y. Studies on development of sufficiently chemoselective N-acylation reagents: N-acyl-N-(2,3,4,5,6-pentafluorophenyl)-methanesulfonamides. Tetrahedron 2000, 56, 5843-5856;
21. (d) Burger, A.; Hornbaker, E.D. Some aromatic trifluoromethyl derivatives. The Rosenmund reduction of trifluoromethyl benzoic acids. J. Org. Chem. 1953, 18, 192-195;
22. (e) Mastrukova, T.A.; Sheinker, Y.N.; Kuznetsova, I.K.; Peresleni, E.M.; Sakharova, T.B.; Kabachnik, M.I. The application of the Hammett equation to the theory of tautomeric equilibrium-II: Tautomerism of α- arylsulphaminopyridines. Tetrahedron 1963, 19, 357-372;
23. (f) Kaplan, H.; Leubner, G.W. Some halogenated sulfonanilides. J. Am. Chem. Soc. 1945, 67, 1076-1077;
24. (g) Courts, I.G.C.; Edwards, M.; Richards, D.J. Mild selective hydrolysis of the methyl esters of some ortho-substituted aromatic carboxylic acids. Synthesis 1981, 487-489;
25. (h) Weisblat, D.I.; Magerlein, B.J.; Hanze, A.R.; Myers, D.R.; Rolfson, S. Synthesis of pteroic and pteroylglutamic acids. J. Am. Chem. Soc. 1953, 75, 3625-3629;
26. (i) Hu, H.; Mendoza, J.S.; Lowden, C.T.; Ballas, L.M.; Janzen, W.P. Synthesis and protein kinase C inhibitory activities of balanol analogs with modification of 4-hydroxybenzamido moiety. Bioorg. Med. Chem. 1997, 5, 1873-1882.