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  • Title: Radical cyclization in heterocycle synthesis 15. Relationship between a Radical species and radical acceptors of three different types of double bond in radical addition-cyclization.
    Author: Miyata O, Kajisa S, Ueda M, Yamauchi M, Naito T.
    Journal: Chem Pharm Bull (Tokyo); 2005 Aug; 53(8):995-1002. PubMed ID: 16079534.
    Abstract:
    Relationship between a radical species and radical acceptors of three different types of double bond in radical addition-cyclization was systematically investigated. Substrates carrying alpha,beta-unsaturated amide, isolated olefin, and oxime ether moieties underwent radical addition-cyclization to give differently substituted lactams depending upon the radicals used. The sulfanyl radical addition-cyclization of the substrate proceeded smoothly to give the 5-membered lactam having an alkoxyamino group as a result of preferable addition of an intermediary alpha-carbonyl radical to the oxime ether. On the other hand, the triethylborane-mediated radical addition-cyclization gave the lactam bearing an iodomethyl group as a result of addition to an intermediary alpha-carbonyl radical to isolated olefin. The different regioselectivity was explained by the stability of the intermediary radical and the interaction between SOMO and HOMO.
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