N-(Chlorosulfonyl)imidoyl chlorides react regioselectively with anilines, 2-aminomethylnaphthaline, or 1,2,3,4-tetrahydroquinoline leading to derivatives of 1,2,4-benzothiadiazine 1,1-dioxide. Heterocyclization occurs at the sterically less hindered C-6 atom in the case of 3-methoxy- and 3,4-dimethoxyaniline, while the reaction with 3-methylaniline leads to a mixture of cyclization products at the C-2 and C-6 atoms of aniline.
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Corena, M.; Linser P. J. WO Patent 2005107470.
Tedesco, R.; Shaw, A. N.; Bambal, R.; Chai, D.; Concha, N. O.; Darcy, M. G.; Dhanak, D.; Fitch, D. M.; Gates, A.; Gerhardt, W. G.; Halegoua, D. L.; Han, C.; Hofmann, G. A.; Johnston, V. K.; Kaura, A. C.; Liu, N.; Keenan, R. M.; Lin-Goerke, J.; Sarisky, R. T.; Wiggall, K. J.; Zimmerman, M. N.; Duffy, K. J. J. Med. Chem. 2006, 49, 971.
Ruebsam, F.; Murphy, D. E.; Tran, C. V.; Li, L.-S.; Zhao, J.; Dragovich, P. S.; McGuire, H. M.; Xiang, A. X.; Sun, Z.; Ayida, B. K.; Blazel, J. K.; Kim, S. H.; Zhou, Y., Han, Q.; Kissinger, C. R.; Webber, S. E.; Showalter, R. E.; Shah, A. M.; Tsan, M.; Patel, R. A.; Thompson, P. A.; LeBrun, L. A.; Hou, H. J.; Kamran, R.; Sergeeva, M. V.; Bartkowski, D. M.; Nolan, T. G.; Norris, D. A.; Khandurina, J.; Brooks, J.; Okamoto, E.; Kirkovsky, L. Bioorg. Med. Chem. Lett. 2009, 19, 6404.
Monzani, A.; Di Bella, M.; Fabio, U.; Manicardi, G. Farmaco 1973, 28, 149.
Ivanova, E. M.; Borovika, D. A.; Vozny, I. V.; Trapencieris, P.; Žalubovskis, R. Chem. Heterocycl. Compd. 2012, 48, 1114. [Khim. Geterotsikl. Soedin. 2012, 1194.]
Inokuma, T.; Furukawa, M.; Uno, T.; Suzuki, Y.; Yoshida, K.; Yano, Y.; Matsuzaki, K.; Takemoto Y. Chem.–Eur. J. 2011, 17, 10470.
(a) Fedenko, V. S.; Solomko, Z. F.; Avramenko, V. I. Chem. Heterocycl. Compd. 1984, 20, 735. [Khim. Geterotsikl. Soedin. 1984, 907.] (b) Topliss, J. G.; Sherlock, M. H.; Reimann, H.; Konzelman, L. M.; Shapiro, E. P.; Pettersen, B. W.; Schneider, H.; Sperber, N. J. Med. Chem. 1963, 6, 122.
Fallon, G. D.; Jahangiri, S.; Liepa, A. J.; Woodgate, R. C. Aust. J. Chem. 2005, 58, 332.
Cablewski, T.; Forsyth, C. M.; Francis, C. L.; Liepa, A. J.; Tran, V. Aust. J. Chem. 2008, 61, 785.
Cablewski, T.; Francis, C. L.; Liepa, A. J. Aust. J. Chem. 2007, 60, 113.
(a) Forsyth, C. M.; Francis, C. L.; Jahangiri, S.; Liepa, A. J.; Perkins, M. V.; Young, A. P. Aust. J. Chem. 2010, 63, 659. (b) Forsyth, C. M.; Francis, C. L.; Jahangiri, S.; Liepa, A. J.; Perkins, M. V.; Young, A. P. Aust. J. Chem. 2010, 63, 785.
Fallon, G. D.; Craig, L.; Johansson, F. K.; Liepa, A. J.; Woodgate, R. C. J. Aust. J. Chem. 2005, 58, 891.
Norman, R. E.; Perkins, M. V.; Liepa, A. J.; Francis, C. L. Aust. J. Chem. 2013, 66, 1323.
Markovskii, L. N.; Shermolovich, Y. G.; Shevchenko, V. I. J. Org. Chem. USSR 1974, 10, 492. [Zh. Org. Khim. 1974, 10, 488.]
Schröder, H.; Fischer, E.; Michalik, M.; Oehme, G. J. Prakt. Chem. 1988, 330, 900.
Markovskii, L. N.; Shermolovich, Y. G.; Shevchenko, V. I. J. Org. Chem. USSR 1973, 9, 644. [Zh. Org. Khim. 1973, 633.]
Foubister, A. J.; Sloam, A. D. B. Chem. Ind. 1970, 1, 27.
Cronin, T. H.; Hess, H. J. J. Med. Chem. 1968, 11, 136.
Nagarajan, K.; Bhat, G. A.; Rao, V. R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1992, 31B, 310.
Schläpfer-Dähler, M.; Heimgartner, H. Helv. Chim. Acta 1993, 76, 2398.
Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W. CRYSTALS. Issue 10; Chemical Crystallography Laboratory, University of Oxford: Oxford, 1996.
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Deceased (Anatoly D. Sinitsa).
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(4), 267–274
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Shalimov, A.A., Chudakova, T.I., Vlasenko, Y.G. et al. Heterocyclization of N-(chlorosulfonyl)imidoyl chlorides with anilines, a new method of synthesis of 1,2,4-benzothiadiazine 1,1-dioxides. Chem Heterocycl Comp 52, 267–274 (2016). https://doi.org/10.1007/s10593-016-1873-z
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DOI: https://doi.org/10.1007/s10593-016-1873-z