Abstract
The reactions of 2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione with dimethyl sulfate, benzyl chloride, and allyl bromide afforded the corresponding 2-alkyl-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-triones and 3-(alkoxy)-6,11-dihydroanthra[2,1-d]isothiazole-6,11-diones. The reactions of 2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione and its S-oxide with a formaldehyde—secondary amine system yielded 2-[(alkylamino)methyl]-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-triones and 2-[(alkylamino)methyl]-3,6,11-trioxo-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole 1-oxides, respectively.
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F. A. Kucherov and S. G. Zlotin, Izv. Akad. Nauk, Ser. Khim., 2001, 1580 [Russ. Chem. Bull., Int. Ed., 2001, 50, 1657].
S. G. Zlotin, P. G. Kislitsin, A. I. Podgursky, A. V. Samet, V. V. Semenov, A. C. Buchanan III, and A. A. Gakh, J. Org. Chem., 2000, 65, 8439.
C. Flouzat, Y. Bresson, A. Mattio, J. Bonnet, and G. Guillaumet, J. Med. Chem., 1993, 36, 497.
M. R. Borenstein, M. A. Abou-Gharbia, and P. H. Doukas, Heterocycles, 1984, 22, 2433.
E. D. Weiler and G. A. Miller, J. Het. Chem., 1976, 13, 1097.
H. Zinner, U. Zelck, and G. Rembarz, J. Prakt. Chem., 1959, 8, 150.
E. A. Serebryakov, P. G. Kislitsyn, S. G. Zlotin, and V. V. Semenov, Synthesis, 2001, 11, 1659.
?. J. Gordon and R. A. Ford, The Chemist´s Companion, J. Wiley and Sons, New York-London-Sydney-Toronto, 1972.
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Kucherov, F.A., Zlotin, S.G. Alkylation of 2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione and its S-oxide. Russian Chemical Bulletin 52, 755–758 (2003). https://doi.org/10.1023/A:1023947931841
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DOI: https://doi.org/10.1023/A:1023947931841