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Issue 19, 1994
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Polyaza heterocycles. Part 2. Nucleophilic substitution of halogens in halogenoquinoxalino[2,3-c]cinnolines

Abstract

10-Chloroquinoxalino[2,3-c]cinnoline readily undergoes methoxydechlorination when treated with sodium methoxide. The 1-, 2-, 3-, 4- and 9-chloro isomers are unreactive towards this reagent, but the 9,10-dichloro derivative undergoes substitution of both chlorines (the 10-position being much the more reactive). The 9- and 10-bromo analogues are both unreactive towards sodium methoxide, but the 9- and 10-fluoro analogues are both highly reactive, to the extent that it has not been possible even to isolate the 10-fluoro compound. Routes to 9- and 10-piperidinoquinoxalino[2,3-c]cinnolines are described.

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Article type: Paper
DOI: 10.1039/P19940002751
J. Chem. Soc., Perkin Trans. 1, 1994, 2751-2758

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    Polyaza heterocycles. Part 2. Nucleophilic substitution of halogens in halogenoquinoxalino[2,3-c]cinnolines

    A. Ahmad, L. J. Dunbar, I. G. Green, I. W. Harvey, T. Shepherd, D. M. Smith and R. K. C. Wong, J. Chem. Soc., Perkin Trans. 1, 1994, 2751
    DOI: 10.1039/P19940002751

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