37773-35-6Relevant articles and documents
Metal-Free Synthesis of Selenodihydronaphthalenes by Selenoxide-Mediated Electrophilic Cyclization of Alkynes
An, Shaoyu,Li, Pingfan,Zhang, Zhong
, p. 3059 - 3070 (2021/07/22)
A transition-metal-free, selenium mediated electrophilic cyclization reaction was realized through a one-pot procedure between simple alkynes and triflic anhydride-activated selenoxides to give selenium containing dihydronaphthalene products. This method gave good to very high yields for all products, including selenium-substituted phenanthrene, dihydroquinoline, 2H-chromene, and coumarin, which can be further transformed to other functionalized compounds.
FeCl3-Diorganyl dichalcogenides promoted cyclization of 2-alkynylanisoles to 3-chalcogen benzo[ b ]furans
Gay, Rafaela M.,Manarin, Flavia,Schneider, Caroline C.,Barancelli, Daniela A.,Costa, Michael D.,Zeni, Gilson
supporting information; experimental part, p. 5701 - 5706 (2010/10/03)
A general synthesis of 3-chalcogen benzo[b]furans from the readily available 2-alkynylanisoles, via FeCl3/diorganyl dichalcogenides intramolecular cyclization, has been developed. Aryl and alkyl groups directly bonded to the chalcogen atom were used as cycling agents. The results revealed that the reaction significantly depends on the electronic effects of substituents in the aromatic ring bonded to the selenium atom of the diselenide species. We observed that the pathway of reaction was not sensitive to the nature of substituents in the aromatic ring of anisole since both the electron-donating and the electron-withdrawing groups delivered the products in similar yields. In addition, the obtained heterocycles were readily transformed to more complex products by using a chalcogen/lithium exchange reaction with n-BuLi followed by trapping of the lithium intermediate with aldehydes, furnishing the desired secondary alcohols in good yields.
SYNTHESIS, STRUCTURE, AND PROPERTIES OF COMPOUNDS WITH A CHALCOGEN-NITROGEN BOND. V. N-TRIFLUOROACETYL-Se-ARYL-Se-METHYLSELENIMIDES
Naddaka, V. I.,Krasnov, V. P.,Minkin, V. I.
, p. 432 - 436 (2007/10/02)
The IR and UV spectra of a series of N-trifluoroacetyl-Se-aryl-Se-methylselenimides were studied.The molecules of these compounds, like those of N-acylsulfimides and N-acyltelurimides with similar structures, have a bipolar structure, in which the negative charge is distributed through the bond system of the N-trifluoroacetyl group.
