A novel synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors

…, MB Hursthouse, M Nyerges, RJ Anderson…

文献索引：Groundwater, Paul W.; Garnett, Ian; Morton, Andrew J.; Sharif, Toqir; Coles, Simon J.; Hursthouse, Michael B.; Nyerges, Miklos; Anderson, Rosaleen J.; Bendell, David; McKillop, Alexander; Zhang, Weimin Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 21 p. 2781 - 2787

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被引用次数: 8

摘要

Generation of nitrile ylides, 4 and 22, via the base-catalysed 1, 3-dehydrochlorination of imidoyl chlorides, 3 and 21, gives the imidazoles, 13, 23 and 24. These imidazoles are formed by the cycloaddition of the nitrile ylides, 4 and 22, to their precursor imidoyl chlorides, 3 and 21, and the observed regiochemistry of this cycloaddition has been rationalised by energy calculations on the frontier molecular orbitals of these reactants using semi- ...