Modelling One-Pot Method for Synthesis of 2,3-Dihydro-1<i>H</i>-pyrrolo[2,1-<i>c</i>][1,4]benzothiazine 5,5-Dioxides and Their Homologues — Oak Academic Publishing
Research ArticleOpen AccessGoogle Scholar indexed
Modelling One-Pot Method for Synthesis of 2,3-Dihydro-1<i>H</i>-pyrrolo[2,1-<i>c</i>][1,4]benzothiazine 5,5-Dioxides and Their Homologues
National University of Pharmacy, Kharkiv, Ukraine
,
National University of Pharmacy, Kharkiv, Ukraine
,
National University of Pharmacy, Kharkiv, Ukraine
,
National University of Pharmacy, Kharkiv, Ukraine
,
National University of Pharmacy, Kharkiv, Ukraine
,
National University of Pharmacy, Kharkiv, Ukraine
1 National University of Pharmacy, Kharkiv, Ukraine
2 National University of Pharmacy, Kharkiv, Ukraine
3 National University of Pharmacy, Kharkiv, Ukraine
4 National University of Pharmacy, Kharkiv, Ukraine
5 National University of Pharmacy, Kharkiv, Ukraine
6 National University of Pharmacy, Kharkiv, Ukraine
A facile method for synthesis of 2,3-dihydro-1 H -pyrrolo[2,1- c ][1,4]benzothiazines by interaction of methylenactive (2-fluorophenyl)sulfones with homologues of either 5-methoxy-3,4-dihydro-2 H -pyrrole or 5-(methylthio)-3,4-dihydro- 2 H -pyrrole has been developed.
F. Varano, D. Catarzi, V. Colotta, G. Filacchioni, L. Cecchi, A. Galli and C. Costagli, “Synthesis of 2-Substituted-6,8-dichloro-3,4-dihydro-3-oxo-2H-1,4-benzothiazine-1,1-dioxides and -1-Oxides as Glycine-NMDA Receptor Antagonists,” Il Farmaco, Vol. 53, No. 12, 1998, pp. 752-757. doi:10.1016/S0014-827X(98)00097-4
P. Rafferty, D. Calderwood, L. D. Arnold, B. Gonzalez Pascual, J. L. Ortego Matinez, M. J. Perez de Vega and I. F. Fernandez, “Benzothiazinone and Benzoxazinone Compounds,” PCT Int. Appl. WO 2000075139, 2000.
J. F. Blake, J. B.Fell, J. P. Fischer, R. T. Hendricks, J. E. Robinson, S. R. Spencer and P. J. Stengel, “Heterocyclic Antiviral Compounds,” US Patent No. 2006040927, 2006.
H. C. Hansen, T. M. Tagmose and J. B. Hansen, “Fused 1,4-Thiazine-2-carbonitrile Derivatives, Their Preparation and Use,” PCT Int. Appl. WO 2000055147, 2000.
T. Yamamoto, I. Watanabe, K. Harada and S. Ikeda, “Benzo[1,4]thiazine Derivatives and Drugs Comprising the Same,” PCT Int. Appl. WO 9813357, 1998.
I. Iijima, S. Nomura, K. Okumura, K. Takashima and K. Suzuki, Jpn. Kokai Tokkyo Koho JP 04041483,1992.
H. Kano and S. Takahashi, “Shionogi Kenkyusho Nenpo,” Shionogi Kenkyusho Nempo, Vol. 11, No. 1, 1961, pp. 1-3.
G. Fengler, D. Arlt, K. Grohe, H. J. Zeiler and K. Metzger, “4H-1,4-Benzothiazin-Derivate,” Ger. Offen. DE 3229125, 1984.
T. Kachhee, V. Gupta, D. C. Gautam and R. Gupta, “Synthesis of 4H-1,4-Benzothiazine-1,1-dioxides (Sulfones) and Phenothiazine-5,5-dioxides (Sulfones),” Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 180, No. 10, 2005, pp. 2225-2234. doi:10.1080/104265090917790
G. Kumar, V. Gupta, D. Gautam and R. Gupta, “Synthesis of Sulfones OF 4H-1,4-Benzothiazines and Phenothiazines,” Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 179, No. 10, 2004, pp. 1941-1948. doi:10.1080/10426500490466931
V. Molteni, X. He, J. Nabakka, K. Yang, A. Kreusch, P. Gordon, B. Bursulaya, I. Warner, T. Shin, T. Biorac, N. S. Ryder, R. Goldberg, J. Doughty and Y. He, “Identification of Novel Potent Bicyclic Peptide Deformylase Inhibitors,” Bioorganic & Medicinal Chemistry Letters, Vol. 14, No. 6, 2004, pp. 1477-1481. doi:10.1016/j.bmcl.2004.01.014
K. Gupta, B. S. Rathore, R. Gupta, V. Gupta and M. Kumar, “Synthesis and Spectral Studies of 4H-1,4-Benzothiazine S,S-Dioxides (Sulfones),” Heterocyclic Communications, Vol. 9, No. 4, 2003, p. 381.
T. S. Yokum, J. Alsina and G. Barany, “Solid-Phase Syntheses of Heterocycles Containing the 2-Aminothiophenol Moiety,” Journal of Combinatorial Chemistry, Vol. 2, No. 3, 2000, pp. 282-292. doi:10.1021/cc9900854
S. C. Schou, H. C. Hansen, T. M. Tagmose, H. C. M. Boonen, A. Worsaae, M. Drabowski, P. Wahl, P. O. G. Arkhammar, T. Bodvarsdottir, M.-H. Antoine, P. Lebrun and J. B. Hansen, “Synthesis and Pharmacological Evaluation of 4H-1,4-Benzothiazine-2-carbonitrile 1,1-dioxide and N-(2-Cyanomethylsulfonylphenyl)acylamide Derivatives as Potential Activators of ATP Sensitive Potassium Channels,” Bioorganic & Medicinal Chemistry Letters, Vol. 13, No. 1, 2005, pp. 141-155. doi:10.1016/j.bmc.2004.09.051
A. I. Gerasyuto, S. G. Zlotin and V. V. Semenov, “Synthesis of 2,3-Dihydrobenzothiazol-1,1-dioxide and 2,3Dihydro-1,4-benzothiazin-3-one Nitroderivatives from 2,4-Diand 2,4,6-Trinitrobenzamides,” Synthesis, Vol. 2, 2001, pp. 300-304. doi:10.1055/s-2001-10820
F. Babudri, S. Florio, A. M. Vitrani and L. Di Nunno, “Synthesis of 4H-1,4-Benzothiazines via Lithiation Alpha to Sulphur of 2-Acylaminophenyl Alkyl Sulphides, Sulphoxides, and Sulphones,” Journal of the Chemical Society, Perkin Transactions 1, Vol. 8, 1984, pp. 1899-1903. doi:10.1039/p19840001899
Y. Ishikawa, Y. Terao, K. Suzuki, N. Shikano and M. Sekiya, “Cyclization of αand β-Alkylthio-Substituted Amines Possessing Positively Charged Carbon at the Nitrogen. A New Synthetic Method for Thiazolidines, Thiomorpholines and Dihydro-1,4-benzothiazines,” Chemical & Pharmaceutical Bulletin, Vol. 32, No. 2, 1984, pp. 438-446. doi:10.1248/cpb.32.438
G. Pagani, “Ricerche sui Solfoni Ciclici. Nota V. 4H1,4-Benzothiazine-1,1-diossido,” Gazzetta Chimica Italiana, Vol. 97, 1967, pp. 1804-1807.
A. S. Angeloni and G. Pappalardo, “Benzothiazinone Diossidi e Loro Derivati,” Gazzetta Chimica Italiana, Vol. 91, 1961, pp. 633-635.
G. Fengler, D. Arlt and K. Grohe, “4H-1,4-Benzothiazin-derivate,” Ger. Offen. DE 3229124, 1984.
S. E. Lopez, J. Charris, N. Urdaneta and G. Lobo, “Synthesis of N-Aryl Substituted 4H-1,4-Benzothiazine 1,1Dioxide 2-Carboxylic Acid-Esters,” Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 143, No. 1, 1998, pp. 53-61. doi:10.1080/10426509808045484
S. E. Lopez, M. V. Godoy, N. Urdaneta and M. Rosales, “An Improved Procedure for the Preparation of N-Aryl Substituted 4H-1,4-Benzothiazine 1,1-Dioxide Derivatives,” Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 156, No. 1, 2000, pp. 69-80. doi:10.1080/10426500008044994
S. E. Lopez, J. Charris, N. Urdaneta, C. E. Canelon, J. Salazar, J. Herrera and J. E. Angel, “Unexpected Desulfonation OF α-Phenylsulfonyl Enaminoacrylates during Their Cyclisation to New N-Aryl 4H-1,4-Benzothiazinel,l-dioxides,” Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 175, No. 1, 2001, pp. 87-97. doi:10.1080/10426500108040258
S. E. Lopez, J. Salazar, O. Rebollo and J. Restrepo, “A Microwave Induced Cyclisation of α-Phenylsulfonyl-enaminoacrylates for the Preparation of 4-Aryl-4H-1,4-benzothiazine 1,1-Dioxide Derivatives,” Journal of Heterocyclic Chemistry, Vol. 42, No. 5, 2005, pp. 1007-1010. doi:10.1002/jhet.5570420541
J. Charris, A. Barazarte, J. Dominguez and N. Gamboa, “Microwave-Assisted Synthesis of Quinolones and 4H1,4-Benzothiazine 1,1-Dioxides,” Journal of Chemical Research, Vol. 1, No. 2, 2005, pp. 27-28. doi:10.3184/0308234053431158
T. P. Culbertson, “Synthesis of 4H-1,4-Benzothiazine 1Oxide and 1,1-Dioxide. Analogs of Quinolone Antibacterial Agents,” Journal of Heterocyclic Chemistry, Vol. 28, No. 7, 1991, p. 1701.
G. M. Coppola and R. E. Damon, “Novel Heterocycles. 6. The Condensation of Ethyl o-Fluorobenzoyl Acetate with Cyclic Imino Ethers,” Journal of Heterocyclic Chemistry, Vol. 17, No. 8, 1980, pp. 1729-1731. doi:10.1002/jhet.5570170818
L. V. Ershov and V. G. Granik, “Lactams of Acetals and Acid Amides, 45. Synthesis of Condensed 2-Pyridones from Activated Amides, Lactams, and Lactones,” Chemistry of Heterocyclic Compounds, Vol. 21, No. 7, 1985, pp. 771-774. doi:10.1007/BF00519144
S.-I. Hirokami, T. Takahashi, M. Nagata and T. Yamazaki, “Rearrangements of Dewar 4-Pyrimidinones and 4-Methoxy-2-azetidinones. Reactions through Azetidinyl and Acyl Cations,” Journal of Organic Chemistry, Vol. 52, No. 12, 1987, pp. 2455-2468. doi:10.1021/jo00388a022
K. Sukata, “A Simple and Convenient Method for the Synthesis of Sulfones Using Polyethylene Glycols or Their Dialkyl Ethers as Solvents or Catalysts,” Bulletin of the Chemical Society of Japan, Vol. 57, No. 2, 1984, pp. 613-614. doi:10.1246/bcsj.57.613
H. Techer, M. Lavergne and M. Pesson, “Organic Syntheses without Solvent: Preparation of Sulfones and Dithioacetals,” Synthesis, Vol. 1, 1987, pp. 56-59. doi:10.1055/s-1987-27843
J. S. Grossert, P. K. Dubey, G. H. Gill, T. S. Cameron and P. A. Gardner, “The Preparation, Spectral Properties, Structures, and Base-Induced Cleavage Reactions of Some α-Halo-β-ketosulfones,” Canadian Journal of Chemistry, Vol. 62, No. 4, 1984, pp. 798-807. doi:10.1139/v84-133
C. A. Zezza, M. B. Smith, B. A. Ross, A. Arhin and P. L. E. Cronin, “Reaction of Organolithium Reagents with Lactim Ethers: Preparation of Cyclic 2-Alkyl Imines or 2,2Dialkyl Amines,” Journal of Organic Chemistry, Vol. 49, No. 23, 1984, pp. 4397-4399. doi:10.1021/jo00197a013
J. P. Célérier, M. G. Richaud and G. Lhommet, “Imidoylation Reactions: A Simple Direct Synthesis of 3-Amino2-alkenoic Esters (β-Enaminoesters),” Synthesis, Vol. 3, 1983, pp. 195-197. doi:10.1055/s-1983-30276