Synthesis of 6-alkylthioimidazo[1,2-a]pyridines
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A number of 6-alkylthio(and sulfonyl)-substituted imidazo[1,2-a]pyridines were synthesized by the reaction of 5-alkylthio- and 5-alkylsulfonyl-2-aminopyridines with ω-bromoacetophenone and α-chlorocyclohexanone in order to search for new compounds that have fungicidal activity. 5-Alkylthio-2-aminopyridines were obtained from the double salt of 5-mercapto-2-aminopyridine with SnCl2 and HCl by reaction with alkyl halides or tert-C4H9OH and 75% H2SO4. 5-tert-Butylthio-2-aminopyridine was oxidized by means of KMnO4 to 5-tert-butylsulfonyl-2-aminopyridine. A double salt was synthesized from 2-aminopyridine-5-sulfonic acid.
KeywordsOrganic Chemistry Pyridine H2SO4 Halide KMnO4
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