Isoquinoline reacts with potassium cyanide and sulphuryl chloride to give, depending upon the reaction conditions, 4-chloro-1-cyano-, 1,3-dicyano-, 1-aminocarbonyl-3-cyano-, 3-cyano-, and 1-cyano-isoquinoline, thus illustrating a simple method for the direct introduction of chloro- and cyano-substituents into nitrogen heterocycles.
G. W. Kirby, S. L. Tan and B. C. Uff, J. Chem. Soc. D, 1969, 1075a DOI: 10.1039/C2969001075A
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