Synthesis of 1-ethyl-1H-2,1-benzothiazine 2,2-dioxide derivatives using cycloalkanecarbaldehydes and evaluation of their antimicrobial activity

4,6-Dihydropyrano[3,2- c ][2,1]benzothiazine 5,5-dioxides were synthesized via three-component interaction of 1-ethyl-1 H -2,1-benzothiazin-4(3 H )-one 2,2-dioxide with active methylene nitriles and cycloalkanecarbaldehydes. The latter were also applied to obtain ammonium salts of 3,3'-(cycloal...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2017-02, Vol.53 (2), p.219-229
Main Authors: Lega, Dmitry A., Chernykh, Valentine P., Zaprutko, Lucjusz, Gzella, Andrzej K., Shemchuk, Leonid A.
Format: Article
Language:English
Subjects:
Ammonium salts
Antiinfectives and antibacterials
Chemistry
Chemistry and Materials Science
Dioxides
Fungicides
Nitriles
NMR
Nuclear magnetic resonance
Organic Chemistry
Pharmacy
Single crystals
Synthesis
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Summary:4,6-Dihydropyrano[3,2- c ][2,1]benzothiazine 5,5-dioxides were synthesized via three-component interaction of 1-ethyl-1 H -2,1-benzothiazin-4(3 H )-one 2,2-dioxide with active methylene nitriles and cycloalkanecarbaldehydes. The latter were also applied to obtain ammonium salts of 3,3'-(cycloalkylmethanediyl)bis(1-ethyl-1 H -2,1-benzothiazin-4-ol) 2,2,2',2'-tetraoxides. The structures of the synthesized compounds were confirmed by 1 H, 13 C NMR as well as mass spectral and elemental analysis data. The structures of two representatives from each class of the target compounds have been additionally confirmed by single crystal X-ray diffraction study. The synthesized compounds were screened for antibacterial and antifungal activities.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-017-2043-7