Examples of the possibility of easy nucleophilic substitution of the chlorine in the derivatives 3

February 23, 2024

• Title:       

  Examples of the possibility of easy nucleophilic substitution of the chlorine in the derivatives 3

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  Chlorotrimethylsilane-mediated friedlaender synthesis of 2-(α-chloroalkyl)quinoline derivatives

• Mark:

  Scheme 1

• Associated context:

  The possibility of easy nucleophilic substitution of the chlorine in the derivatives 3 was demonstrated by several examples (Scheme 1). Thus, the nitriles 5a–c were prepared by the reaction of compounds 3a–c with potassium cyanide. Treatment of the derivatives 3a–d with secondary amines and mercaptanes yielded the corresponding quinolines 6a–d. Finally, reaction of the chloroesters 3a,b with the nucleophiles containing primary amino group afforded the expected lactams 7a,b. All these substitution reactions occurred in almost quantitative yields.