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

Cycloalkanecarbaldehydes in synthesis of novel 1,2-benzoxathiin-4(3H)-on 2,2-dioxide derivatives and study of the antimicrobial activity of synthesized compounds

“…3). The first one comprises the formation of Michael adduct F which looses the molecule of ethyl cyanoacetate and is converted into enone G, that gives triethylammonium salt according to what was reported previously [6]. The second possible way involves the formation of enone G by direct interaction of 1,2benzoxathiin-4(3H)-on 2,2-dioxide 1 with aldehyde 3c, that next reacts with the second molecule of 1 forming symmetrical bis-derivative isolated as triethylammonium salt 5c.…”

“…Formation of such pharmacologically interesting compounds type as triethylammonium salts and previously reported results devoted to the two-component reaction of 1H-2,1-benzothiazin-4-on 2,2-dioxide with cycloalkanecarbaldehydes [6] encouraged us to continue these investigations and to study similar interaction for 1,2-benzoxathiin-4(3H)-on 2,2-dioxide.…”

“…Considering the previous research of the interaction of 1H-2,1-benzothiazin-4-on 2,2-dioxide with active methylene nitriles and cycloalkanecarbaldehydes [6] we began our investigation from the studying of the reaction of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide 1 with malononitrile 2 and cyclopropanecarbaldehyde 3a.It was discovered, that as in the previous case, the reaction proceeded under room temperature in ethanol with the presence of catalytic amount of triethylamine and resulted into the formation of 2-amino-4-cyclopropyl-4,6dihydropyrano[3,2-c][2,1]benzoxathiin-3-carbonitrile 5,5-dioxide 4a in 55 % yield (Scheme 2). The same reaction conditions were successfully applied for cy-clopentane-and cyclohexanecarbaldehydes 3b and 3c respectively.…”

“…Previously we reported the utilization of 1H-2,1benzothiazin-4-on 2,2-dioxide in 2-amino-4H-pyrans synthesis [5,6]. This "newcomer" turned out to be the prospective core structure for such interactions due to the presence of SO 2 CH 2 CO moiety.…”

Synthesis and biological activity of novel benzoazoles, benzoazines and other analogs functionalized by 2,4-dihydroxyphenyl moiety

“…The representatives of this heterocyclic class are assumed to possess biological activities since they might provide the heteroatoms as potential hydrogen bond acceptors and the fused phenyl ring for possible p-p interactions. In particular, 1,2-benzothiazine and 1,3-benzothiazine derivatives have exhibited promising pharmacological properties: anti-inflammatory, antitumor and antiproliferative activity [3,4], as well as antomicrobial activity [5][6][7][8]. 4H-1,4-benzothiazines exhibited antifungal potency against Aspergillus fumigates and Candida albicans [9,10].…”