Synthesis of 4-octyl-2H-1,4-benzo-thiazin-3-ones

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

“…3-Aryl-and 3-alkyl-4H-benzo[b] [1,4]thiazine-4-carbonitriles 2 (Figure 1) were synthesized in high yield from the corresponding 2-aminobenzothiazoles using the copper-organic framework Cu-MOF-74 as a catalyst [19]. The reactions of 2-aminobenzenethioles with ethyl 2-bromoalkanoates [20], 2-chloroacetic acid [21,22], or diethyl 2-bromo-2-methylmalonate [23] gave 2H-benzo[b] [1,4]thiazin-3(4H)-one deriva-tives 3 (Figure 1), which also have interesting biological properties. 2H-Benzo-1,4-thiazin-3(4H)-ones were also prepared by cyclization of 1,2-diaryldisulfanes with dialkyl but-2-ynedioates [24,25].…”

Microwave-assisted synthesis of optically active N-substituted 2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-ones and -thiazin-3(4H)-ones via Smiles rearrangement

“…14 Moreover, certain kinds of benzo [1,4]oxazin-3(4H)-ones are of interest as photochromic compounds, 15,16 and some possess herbicidal properties. 17 Benzo[b] [1,4]thiazin-3(4H)-ones exhibit different pharmacological activities: bacteriostatic, 18 antimicrobial, 19 antifungal, 20,21 Na + /H + exchange-system inhibitor, 22 and calcium antagonist. [23][24][25] For example, levosemotiadil (Figure 1), an S-enantiomer of semotiadil, is an antiarrhythmic drug that blocks sodium and calcium channels.…”

Synthesis and in vitro antimicrobial activity of benzo[b][1,4]thiazin-3(4H)-ones via smiles rearrangement

“…They also exhibit other different pharmacological activities: bacteriostatic (Guarda et al, 2003), antimicrobial (Guarda et al, 2001;Pitzurra et al, 1999;Fringuelli et al, 1998), Na ? /H ?…”