Abstract
6-Halogeno-8-nitroquinaldies (III, IV, V) were synthesized by the reaction of 4-halogeno-2-nitroanilines with crotonaldehyde, in the presence of Sulfo-mix, boric acid, and ferrous sulfate. The nitroquinaldines were reduced with stannous chloride and hydrochloric acid to 8-amino-6-halogenoquinaldines (VI, IX, X). Under some reaction conditions, dichloro compounds (VII and VIII) were obtained. Thiocyanation of VI, VIII, IX, and X with ammonium thiocyanate and bromine in acetic acid solution gave the thiocyanated compounds (XI to XIV). Thiocyanation of VI to IX was examined by Huckel's molecular orbital method and a good agreement was seen between the theoretical and experimental result.
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Schedule a callMore From: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
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