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A straightforward double intramolecular cyclization of dibenzyl dichalcogenols into a triple bond
Authors:Haruki Sashida  Mamoru Kaname  Akemi Nakayama  Hirokazu Suzuki  Mao Minoura
Affiliation:1. Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan;2. Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, minami-ku, Sagamihara, Kanagawa 252-0373, Japan
Abstract:The intramolecular cyclizations of four types of dibenzyl chalcogenols, which contained one or two ethynyl groups, were carried out. Either the double 5-exo or 6-endo-dig mode ring closure reaction regio- and stereoselectively proceeded to give the corresponding symmetrical bis(benzo[c]chalcogenophene) or bis(isochromene) derivatives from the dibenzyl chalcogenols having a diyne moiety. In contrast, the regioselective tandem 5-exo-dig mode intramolecular ring closure reactions of dibenzyl thiol and selenol having a mono-yne into a triple bond gave the trans-biisobenzothiophene and selenophene as the sole product. However, the similar cyclization of dibenzyl tellurol proceeded in both tandem 5-exo and 6-endo-dig modes to afford the trans-biisobenzotellurophene and ditellurachrysene in good yields with the ratio of 1:1. The X-ray structural analysis of these novel compounds is also presented.
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