Synthesis of (dihydrobenzoxathiinyloxy)acetic acids

Abstract

Several (dihydrobenzoxathiinyloxy)acetic acids have been prepared as potential antihypertensive agents. The dihydrobenzoxathiin ring system was constructed via an intramolecular alkoxide displacement reaction.

Copper(I)-BINOL Catalyzed Domino Synthesis of 1,4-Benzoxathiines through -O Bond Formation

“…Particularly the compounds containing 1,4benzoxathiine motifs have attracted considerable interest during the past few years due to their interesting biological activities [5][6][7][8]. Framework of 1,4-benzoxathiine is present in a variety of biologically active compounds such as (3hydroxy-4-methoxyphenyl)-1,4-benzoxathiine 1, a sweetening agent [9]; (dihydrobenzoxathiinyloxy)acetic acids 2, potential antihypertensive agents with diuretic properties [10]; syn-2,3-bis-aryl-substituted dihydrobenzoxathiine 3, an estrogenic agent [11]; hydroxy substituted 4-thiaflavan 4, an antioxidant agent [12] (Figure 1). 1,4-Benzoxathiine motifs are also used as radical scavengers [13]; metal chelators [14]; and hydroperoxide quenchers [15].…”

“…Conventionally, 1,4-benzoxathiine motifs are synthesized by the treatment of 2-mercaptophenol with 1,2dibromoethane in presence of sodiumethoxide [16]. 1,4benzoxathiine moieties are also synthesized by multistep reaction [9,10]. Nair et al, described the synthesis of 1,4-benzoxathiine moiety by the cycloaddition reaction of 4-isopropyl-2-thio-1,2-benzoquinone which is generated in situ from N-(2-hydroxy-5-isopropylphenylsulfanyl)phthalimide with the reaction of alloocimene in the presence of pyridine in dry chloroform [17].…”

Synthesis of β-functionalized ethyl polyfluoroaryl sulfides, sulfoxides, and sulfones underlain by pentafluorobenzoic acid

“…In their turn the syntheses of compounds contain-ing sulfur in the oxidized state (sulfoxide or sulfone) are performed commonly by the oxidation of the sulfide unit of the already formed heterocycle [2,3,5,23]. This fact provides certain limitations for the preparation by this procedure of compounds containing easily oxidizable groups.…”

“…Other ways to 2,3-dihydro-1,4-benzothiazine derivatives were also described [15,16,20]. 2,3-Dihydro-1,4-benzoxathiynes are prepared by the reductive cyclization of o-oxyarylthioketones [5,21], by the addition of o-mercaptophenol to α,β-unsaturated ethers [14], by Diels-Alder heteroreaction of o-thioquinone with vinyl compounds [22], or by intramolecular alkoxydechlorination of S-(2'-hydroxyethyl)-2-chlorothiophenol derivatives [23]. The syntheses of 2,3-dihydro-1,4-benzodithiynes involve the reactions of benzopentathiepines with unsaturated compounds [24], cyclohexanone or cyclohexenone with 1,2-ethanedithiol in the presence of 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide [25], and also intramolecular cyclization of 2-phenylsulfanylethylthiosulfonates or the reactions of dithiopyrocatechol derivatives with 1,2-dibromoethane [26].…”

Facile three-component synthesis of dithiocarbamate derivatives with potent antimicrobial activity

“…There are few general approaches involving amines, carbon disulfide and alkyl halide, epoxide or Michael acceptors to afford dithiocarbamates 1-6 which have demonstrated a broad spectrum of applications including agrochemical, medicinal, and rubber industry. [7][8][9][10] On the other hand, phenoxathiin derivatives were found to be active as potential antihypertensive, 11 antimicrobial, 12,13 antitumour 14 and anti-inflammatory agents 15 and have promising fluorescent properties. 16,17 Several phenoxathiin pyridinium derivatives were prepared and acted as effective antifungal agents against Aspergillus and Candida.…”