Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

An Efficient Synthesis of 2-Alkyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides

  • Published : 2005.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

An efficient and environment friendly method has been described for the synthesis of various 2-alkyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides starting from N-alkylation of sodium obenzosulfimide in an ionic liquid for the first time. Ring cleavage and ring closure of the resulting product were achieved in a single step in a cost effective solvent (methanol) followed by N-alkylation of resulting alkyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate in ionic liquid while boron triflouride was used as a catalyst along with molecular sieves in carboxamide formation step.

Keywords

References

  1. Hanson, P. R.; Probst, D. A.; Robinson, R. E.; Yau, M. Tetrahedron Lett. 1999, 40, 4761 https://doi.org/10.1016/S0040-4039(99)00878-3
  2. Moree, W. J.; Van der Marel, G. A.; Liskamp, R. M. Tetrahedrn Lett. 1991, 32, 409 https://doi.org/10.1016/S0040-4039(00)92641-8
  3. Rough, W. R.; Gwaltney, S. L.; Cheng, J.; Scheidt, K. A.; McKerrow, J. H.; Hansell, E. J. Am. Chem. Soc. 1998, 120, 10994 https://doi.org/10.1021/ja981792o
  4. Ahn, K. H.; Ham, C.; Kim, S.-K.; Cho, C.-W. J. Org. Chem. 1997, 62, 7047 https://doi.org/10.1021/jo970917p
  5. Oppolzer, W.; Kingma, A. J.; Pillai, S.-K. Tetrahedrn Lett. 1991, 32, 4893 https://doi.org/10.1016/S0040-4039(00)93489-0
  6. Gennarti, C.; Salom, B.; Potenza, D.; Williams, A. Angew. Chem. Int. Ed. Engl. 1994, 33, 2067 https://doi.org/10.1002/anie.199420671
  7. Lombardino, J. G.; Wiseman, E. H.; Mclamore, W. J. Med. Chem. 1971, 14, 1171 https://doi.org/10.1021/jm00294a008
  8. Braun, J. Chem. Ber. 1923, 56, 2332 https://doi.org/10.1002/cber.19230561024
  9. Abe, K.; Yammamoto, S.; Matsui, K. Yakagaku Zasshi 1956, 76, 1058
  10. Soler, J. E. US Patent 1985, 4,563,452
  11. Marfat, A. In Annual Drug Report 1987, 202
  12. US Patent 1985, 4,551,452
  13. Turck, D.; Busch, U.; Heinzel, G.; Narjes, H.; Nehmiz, G. Clin. Drug. Invest. 1995, 9, 270 https://doi.org/10.2165/00044011-199509050-00004
  14. Trummlitz, G.; Engel, W.; Seeger, E.; Engelhardt, G. US Patent 1980, 4,233,299
  15. Caruso, I.; Montrone, F.; Boari, L. Adv. Ther. 1994, 11, 132
  16. Gabriel, S.; Colman, J. Ber. 1900, 33, 980, 996, 2630 https://doi.org/10.1002/cber.190003302209
  17. Gabriel, S.; Colman, J. Ber. 1902, 35, 2421 https://doi.org/10.1002/cber.190203502222
  18. Hill, J. H. M. J. Org. Chem. 1965, 30, 620 https://doi.org/10.1021/jo01013a078
  19. Unverferth, K.; Laben, G.; Gunther, W.; Lohmann, D.; Kretzschmar, E.; Kassebaum, H.; Lucke, L.; Jassmann, E.; Hilger, H.; Runge, H. J. Ger. (G. D. R) 1983, 247672
  20. Chem. Abstr. 1988, 108, 150061
  21. Patek, M.; Hampl, F. Collect. Czech. Chem. Comm. 1989, 54, 3267 https://doi.org/10.1135/cccc19893267
  22. Manjarrez, N.; Perez, H. I.; Solis, A. Rev. Mex. Ciencias Farmaceuticas 1995, 25, 20
  23. Welten, T. Chem. Rev. 1999, 99, 2071 https://doi.org/10.1021/cr980032t
  24. Wasserchid, P.; Keim, W. Angew. Chem. Int. Ed. 2000, 39, 3772 https://doi.org/10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
  25. Sheldon, R. Chem. Commun. 2001, 2399
  26. Gordon, C. M. Appl. Catal. A: Chem. 2001, 222, 101 https://doi.org/10.1016/S0926-860X(01)00834-1
  27. Olivier-Bourbigou, H.; Magna, I. J. Mol. Catal. A: Chem. 2002, 182, 419 https://doi.org/10.1016/S1381-1169(01)00465-4
  28. Zhao, D.; Wu, M.; Kou, Y.; Min, E. Catal. Today 2002, 74, 157 https://doi.org/10.1016/S0920-5861(01)00541-7
  29. Ionic Liquid in Synthesis; Wessercheid, P.; Welton, T., Eds.; VCHWiley: Weinheim, 2002
  30. Le, Z. G.; Chen, Z. C.; Hu, Y.; Zheng, Q. G. Synthesis 2004, 208
  31. Owens, G. S.; Abu-Omer, M. M. J. Mol. Catal. A: Chem. 2002, 187, 211

Cited by

  1. Three-Component Reaction: Synthesis, Characterization, and Biological Study of Some Fused Bridgehead Nitrogen Heterocyclic Systems Containing 4-Methylthiophenyl Moiety vol.186, pp.3, 2011, https://doi.org/10.1080/10426507.2010.506454
  2. Piperidine-mediated synthesis of thiazolyl chalcones and their derivatives as potent antimicrobial agents vol.48, pp.5, 2011, https://doi.org/10.1002/jhet.707
  3. ,2-benzothiazine-3-carboxylate vol.67, pp.7, 2011, https://doi.org/10.1107/S1600536811020289
  4. Effect of Substituents on the Regioselectivity of the Reaction of α-Tosyloxyketones with Thioureas in Acidic Medium: Access to 2-Aminothiazoles and 2-Imino-2,3-dihydrothiazoles vol.51, pp.3, 2014, https://doi.org/10.1002/jhet.1676
  5. ]-[1,2,4]-triazoles pp.0022152X, 2013, https://doi.org/10.1002/jhet.1600
  6. Studies on Synthesis of Novel Triazole Tagged Pyrazole Fused Naphthalene 5-Thiazine-5,5-dioxide Derivatives, Their Antimicrobial, and Antioxidant Activity vol.51, pp.S1, 2014, https://doi.org/10.1002/jhet.2013
  7. -1,2-benzothiazin-4-ylidene]acetic acid vol.70, pp.6, 2014, https://doi.org/10.1107/S1600536814008903
  8. )-3,4-Diphenyl-2,3-dihydro-1,3-thiazol-2-ylidene]-2-[1-(4-hydroxyphenyl)ethylidene]hydrazinium bromide including an unknown solvate vol.70, pp.6, 2014, https://doi.org/10.1107/S1600536814010125
  9. -1,2-benzothiazin-4-ylidene]acetic acid vol.70, pp.7, 2014, https://doi.org/10.1107/S1600536814013245
  10. One-pot multicomponent synthesis of novel thiazolylhydrazone derivatives and their antimicrobial activity vol.41, pp.12, 2015, https://doi.org/10.1007/s11164-015-1959-8
  11. Synthesis and anticonvulsant activities of novel 2-(cyclopentylmethylene)hydrazinyl-1,3-thiazoles in mouse models of seizures vol.31, pp.6, 2016, https://doi.org/10.3109/14756366.2016.1158172
  12. Solvent-Free Regioselective Synthesis of Novel Isoxazoline and Pyrazoline N-Substituted Saccharin Derivatives Under Microwave Irradiation vol.52, pp.1, 2016, https://doi.org/10.1007/s10593-016-1828-4
  13. 1,3,4-Thiadiazoles and 1,3-thiazoles from one-pot reaction of bisthioureas with 2-(bis(methylthio)methylene)malononitrile and ethyl 2-cyano-3,3-bis(methylthio)acrylate vol.38, pp.1, 2017, https://doi.org/10.1080/17415993.2016.1237637
  14. An evaluation of anion suitability for use in ionic liquids with long-term, high-temperature thermal stability vol.41, pp.16, 2017, https://doi.org/10.1039/C7NJ01788J
  15. -1,2-benzothiazine-3-carboxamides-1,1-dioxides (oxicams) and their analogues vol.47, pp.17, 2017, https://doi.org/10.1080/00397911.2017.1323102
  16. Synthesis and medicinal importance of oxicams and their analogues vol.47, pp.19, 2017, https://doi.org/10.1080/00397911.2017.1350983
  17. Synthesis of novel 2-acetamidothiazoles tethered with 1,2,3-triazole and pyridine pharmacophores pp.10427163, 2018, https://doi.org/10.1002/hc.21447
  18. An innovative and efficient method to synthesize meloxicam in one-step procedure with respect to the green chemistry pp.1735-2428, 2018, https://doi.org/10.1007/s13738-018-1525-6
  19. )-1-(2-(2-(4(dimethylamino) benzylidene) hydrazinyl)-4-methylthiazol-5-yl)ethanone derivatives as ecto-5′-nucleotidase inhibitors vol.5, pp.9, 2018, https://doi.org/10.1098/rsos.180837
  20. One-pot solvent-free synthesis of novel functionalized ethyl 2-(alkylimino)-4-methyl-3-(alkanoyl)-2,3-dihydrothiazole-5-carboxylates vol.65, pp.9, 2018, https://doi.org/10.1002/jccs.201800018
  21. One-pot three-component synthesis of some novel ethyl 3-alkyl-2-thioxo-2,3-dihydrothiazole-4-carboxylates under solvent- and catalyst-free conditions at room temperature vol.39, pp.4, 2018, https://doi.org/10.1080/17415993.2018.1441841
  22. Synthesis of Potential Biologically Active 1,2-Benzothiazin-3-yl-quinazolin-4(3H)-ones vol.54, pp.8, 2006, https://doi.org/10.1248/cpb.54.1175
  23. Synthesis and Antibacterial Activity of Bis[2-amino-4-phenyl-5-thiazolyl] Disulfides vol.55, pp.7, 2007, https://doi.org/10.1248/cpb.55.1014
  24. -pyrazole-4-carboxylic acid vol.64, pp.7, 2008, https://doi.org/10.1107/S1600536808018394
  25. -1,2-benzothiazine-3-carboxylate 1,1-dioxide vol.64, pp.8, 2008, https://doi.org/10.1107/S1600536808019156
  26. ′-(2,4-Dinitrophenyl)acetohydrazide vol.64, pp.8, 2008, https://doi.org/10.1107/S1600536808019685
  27. -(4-Chloro-2-nitrophenyl)methanesulfonamide vol.64, pp.10, 2008, https://doi.org/10.1107/S1600536808031048
  28. -(methylsulfonyl)acetamide vol.64, pp.11, 2008, https://doi.org/10.1107/S1600536808032157
  29. 2-(Benzenesulfonamido)acetic acid vol.64, pp.12, 2008, https://doi.org/10.1107/S1600536808035721
  30. -1,2-benzothiazin-3-yl)ethanone vol.64, pp.5, 2008, https://doi.org/10.1107/S1600536808007721
  31. -1,2-benzothiazine-3-carboxamide 1,1-dioxide vol.65, pp.4, 2009, https://doi.org/10.1107/S1600536809010058
  32. Methyl 2-(benzenesulfonamido)acetate vol.65, pp.6, 2009, https://doi.org/10.1107/S160053680901616X
  33. -1,2-benzothiazine-3-carboxylate 1,1-dioxide vol.66, pp.5, 2010, https://doi.org/10.1107/S1600536810012365
  34. )-one 1,1-dioxide vol.66, pp.3, 2010, https://doi.org/10.1107/S1600536810005404
  35. )-one 1,1-dioxide vol.66, pp.3, 2010, https://doi.org/10.1107/S1600536810005428
  36. )-one 1,1-dioxide vol.66, pp.3, 2010, https://doi.org/10.1107/S160053681000543X
  37. ′-(3-Methoxybenzylidene)-4-nitrobenzohydrazide monohydrate vol.66, pp.4, 2010, https://doi.org/10.1107/S1600536810010986
  38. An Efficient Synthesis of 2-Alkyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides. vol.37, pp.14, 2005, https://doi.org/10.1002/chin.200614169
  39. Facile α-Ketonization of Carbonyl Compounds Utilizing CuBr2 on Alumina vol.28, pp.5, 2005, https://doi.org/10.5012/bkcs.2007.28.5.871
  40. Facile One-Pot Two-Step Hydroxylation of Alkyl Halides and Alkyl Sulfonates via Acetate Intermediates vol.29, pp.12, 2008, https://doi.org/10.5012/bkcs.2008.29.12.2491
  41. Preparation and evaluation of antibacterial activity of some new 1,2,4-triazole derivatives vol.47, pp.5, 2005, https://doi.org/10.1002/jhet.431
  42. Microwave assisted synthesis and structure-activity relationship of 4-hydroxy-N'-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides as anti-microbial agents vol.46, pp.6, 2005, https://doi.org/10.1016/j.ejmech.2011.03.020
  43. Synthesis, stereochemistry and in vitro antimicrobial evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-4-phenyl-2,3-dihydrothiazoles vol.21, pp.21, 2005, https://doi.org/10.1016/j.bmcl.2011.08.115
  44. Novel 2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides as antioxidant and/or anti-inflammatory compounds vol.66, pp.None, 2005, https://doi.org/10.1016/j.ejmech.2013.06.005
  45. 4‐(4‐Bromophenyl)thiazol‐2‐amine: Crystal structure determination, DFT calculations, visualizing intermolecular interactions using Hirshfeld surface analysis, and DNA binding s vol.32, pp.9, 2005, https://doi.org/10.1002/poc.3968
  46. 2,4,5-Trisubstituted Thiazole: A Privileged Scaffold in Drug Design and Activity Improvement vol.20, pp.None, 2005, https://doi.org/10.2174/1568026620999200917153856
  47. Synthesis, crystal structure, spectroscopic, electronic and nonlinear optical properties of potent thiazole based derivatives: Joint experimental and computational insight vol.1202, pp.None, 2005, https://doi.org/10.1016/j.molstruc.2019.127354
  48. Synthesis and structure confirmation of 2,4-disubstituted thiazole and 2,3,4-trisubstituted thiazole as thiazolium bromide salts vol.151, pp.7, 2005, https://doi.org/10.1007/s00706-020-02640-3
  49. Sodium alginate: Biopolymeric catalyst for the synthesis of 2-amino-4-arylthiazole derivatives in aqueous medium vol.1231, pp.None, 2005, https://doi.org/10.1016/j.molstruc.2021.129900
  50. Pyridine‐2( 1 H )‐thiones: Versatile precursors for one‐pot synthesis of new NICOTINONITRILE‐THIAZOLE hybrids vol.58, pp.7, 2005, https://doi.org/10.1002/jhet.4272
  51. Synthesis, in-vivo anti-diabetic & anticancer activities and molecular modelling studies of tetrahydrobenzo[d]thiazole tethered nicotinohydrazide derivatives vol.15, pp.2, 2005, https://doi.org/10.1016/j.arabjc.2021.103546