A novel strategy yielding a 3-aminothiophene is described herein.This specifically relies upon an a-thiomethylsilane directing deprotonation,thereafter cyclization of the resultant anion into a pendant nitrile forms the necessary 3-aminothiophene ring.During the course of one of our medicinal chemistry programs,the synthesis of 1 was required.Although there are few reports of thieno2,3-6pyridine syntheses in the literature,none allow for the substitution pattern we desired,as indicated in pyridine (1).Herein we report a novel thieno2,3-pyridine synthesis,specifically via a silicon-directed anionic cyclization constructing the thiophene ring.
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