We report herein an alternative method
for the synthesis of seleno-dibenzocycloheptenones
and seleno-spiro[5.5]trienones through the radical cyclization
of biaryl ynones in the presence of diorganyl diselenides, using Oxone
as a green oxidizing agent. The reactions were conducted using acetonitrile
as the solvent in a sealed tube at 100 °C. The protocol is operationally
simple and scalable, exhibits high regioselectivity, and allows the
synthesis of 24 dibenzocycloheptenones/spiro[5.5]trienones in
yields of up to 99%, 17 of which are unpublished compounds. Additionally,
synthetic transformations of the prepared compounds, such as oxidation
and reduction reactions, are demonstrated.
Reactions between 3-amine-2-((pyridin-2-ylmethyl)selanyl)pyridine (L) and MX2 (M = Co, Cu, Zn; X = Cl, Br) result in the formation of the metal(II) molecular complexes 1–5 with the general formula [MX2(L)]....
The reaction between 2,2′‐bis(3‐aminopyridyl) diselenide (L) and metal transition salts results in the formation of molecular or cluster complexes. The structural elucidation of the synthesized complexes [CuCl2(L)] (1), [Cu(3‐NH2PySeO2)2]·2H2O (2), [Cu4(3‐NH2PySe)4]·dimethylformamide (3), [CoCl2(L)] (4), [ZnCl2(L)] (5), and [Ag6(3‐NH2PySe)6] (6) demonstrates the coordination of nitrogen atoms to CuII, CoII, and ZnII, and that of the selenium atoms to CuIand AgI, which agrees with Pearson’s hard and soft acids and bases (HSAB) theory. Furthermore, the oxidation of selenium with the formation of 3‐aminopyridylseleninate [3‐NH2PySeO2]−bonded to the copper atom was observed in complex2. The antimicrobial action of complexes1,2,4, and5was evaluated againstMycobacterium fortuitum,Mycobacterium massiliense, andMycobacterium abscessus.It was observed that all these complexes have potential antimicrobial activity compared with the free ligand and metal salts used in the synthesis.
A monoselenoether ligand (PySeCH2Py) reacts with CoII, CuII, CuI and PdII resulting in the formation of molecular, polymeric or cyclometallated complexes depending on the starting material used and the reaction conditions applied.
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