The study of the three-component interaction between 1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide, heterylcarbaldehydes and active methylene nitriles

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

“…The analysis of the reaction mixture by the 1 H NMR method evidenced the simultaneous formation of the target ethyl 2-amino-4-aryl-4H-pyran-3-carboxylates 115, triethylammonium salts 116 and ethyl α-cyano-β-arylacrylates 117 (Scheme 38). These triethylammonium salts were isolated for the first time in the study on similar interactions involving N-ethyl-1H-2,1-benzothiazin-4(3H)one 2,2-dioxide (nitrogen-containing analogue of compound 1) [54,55]. Thus, it can be assumed that this chemical behavior is a common property of cyclic SO 2 -containing enolnucleophiles having a fragment of XSO 2 CH 2 CO.…”

“…A number of approaches was used by the authors in order to synthesize the target compounds 115 selectively, namely the use of the ethyl cyanoacetate excess (its effectiveness was revealed earlier [55]), different heating modes, the variation of catalysts, as well as the two-component approach [47]. All of them were not successful, but the experiments carried out allowed researchers to propose a possible mechanism of the three-component interaction (Scheme 39).…”

Antimicrobial, anti-inflammatory and analgesic activities of 2-amino-6-ethyl-4,6-dihydropyrano[3,2-c][2,1]benzothiazine 5,5-dioxides and triethylammonium 3-[1-(4-hydroxy-1-ethyl-2,2-dioxido-1h-2,1-benzothiazin-3-yl)-3-(het)arylmethyl]-1-ethyl-1h-2,1-benzo

“…1). Most of them were previously synthesized [23,24]. Moreover, the new 2-amino-3-R-6-ethyl-4,6-dihydropyrano [3,2- in ethanol (5-10 mL) add the catalytic amount of triethylamine.…”

The synthesis, anti-inflammatory, analgesic and antimicrobial activities of ethyl 2-amino-4-alkyl-4,6-dihydropyrano[3,2c][2,1]benzothiazin-3-carboxylate 5,5-dioxides and triethylammonium 3-[(4-hydroxy-1-ethyl-2,2-dioxido-1h-2,1-benzothiazin-3-yl)alkyl]-1-

“…In our previous works [9,10] we showed that application of malononitrile in the threecomponent interaction with 1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide and aldehydes unambiguously led to 2-amino-3-cyano-4H-pyrans condensed with 1-ethyl-1H-2,1-benzothiazine 2,2-dioxide core, while utilization of ethyl cyanoacetate in this reaction was accompanied with side processes and lower yields of target products, namely fused ethyl 2-amino-4H-pyran-3-carboxylates.…”

“…In our previous works [9,10], similar triethylammonium salts were synthesized in high yields via the interaction of 1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide with (het)arylcarbaldehydes (the molar ratio -2:1) in the alcoholic solution in the presence of the equimolar amount of triethylamine. Such conditions were applied for the interaction of 1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide 1 with aliphatic aldehydes 3.…”