Phosphine-Catalyzed Domino Reaction of Thioaurones and Allenoate: Synthesis of Benzothiophene-Fused Dioxabicyclo[3.3.1]nonane Derivatives

The reaction of thioaurone derivatives with allenoate catalyzed by tris­(4-methoxyphenyl)­phosphane (P­(4-MeOC₆H₄)₃) resulted in a domino annulation reaction to produce a benzothiophene-fused bridged bicyclic ring, with 40–91% yields. The advantages of the methodology include diastereoselective formation of a bridged bicyclic ring in a single step, very mild reaction conditions, and success resulting from a broad functional group. The proposed mechanism was tested and supported by DFT calculations

Phosphine-Catalyzed Domino Reaction of Thioaurones and Allenoate: Synthesis of Benzothiophene-Fused Dioxabicyclo[3.3.1]nonane Derivatives

The reaction of thioaurone derivatives with allenoate catalyzed by tris­(4-methoxyphenyl)­phosphane (P­(4-MeOC₆H₄)₃) resulted in a domino annulation reaction to produce a benzothiophene-fused bridged bicyclic ring, with 40–91% yields. The advantages of the methodology include diastereoselective formation of a bridged bicyclic ring in a single step, very mild reaction conditions, and success resulting from a broad functional group. The proposed mechanism was tested and supported by DFT calculations

The distribution map of integrated fluorescence intensity (representing glutathione content) of hRBCs.

<p>A, hRBCs only; B, hRBCs incubating with 6×10⁻⁵ mol L⁻¹ OTC.</p

Effect of OTC on SOD activity of hRBCs.

<p>Data represent the mean ± SD of three independent experiments.</p

Scanning electron micrographs of hRBCs incubated in PBS containing OTC.

<p>The OTC concentration for A, B and C is 0, 1.0×10⁻⁵ mol L⁻¹ and 5.0×10⁻⁵ mol L⁻¹, respectively.</p

Absorption spectra.

<p>(a) supernatant for the hRBCs suspension after centrifugation; (b) hemolysate (incubated with ultrapure water); (c) supernatant for the hRBCs incubated with 1.1×10⁻⁴ mol/L OTC after centrifugation; (d) hemolysate incubated with 4×10⁻⁴ mol/L OTC. a, b, c and d have the same number of hRBCs obtained from the same blood sample.</p

Optical and fluorescence images of hRBCs at 60× magnification (GSH derivatized by NDA).

<p>A and B are the hRBCs under bright field and epifluorescence illumination condition, respectively. C is the derived hRBCs under epifluorescence illumination condition.</p

Effect of OTC on ATPase activity of hRBCs.

<p>Data represent the mean ± SD of three independent experiments.</p

Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α‑Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives

Solvent-controlled switchable domino reactions between 2-alkylidenebenzothiophene-3­(2<i>H</i>)-ones and Morita–Baylis–Hillamn (MBH) carbonate were developed. All domino reactions exhibited excellent regioselectivity, producing a broad spectrum of benzothiophene-fused α-pyran, 2,3-dihydrooxepine, and oxatricyclodecene derivatives. Furthermore, [4 + 2], [4 + 3], and related domino reactions from identical substrates can be controlled

Effect of OTC on GSH-Px activity of hRBCs.

<p>Data represent the mean ± SD of three independent experiments.</p