AlCl3-Catalyzed Intramolecular Cyclization of N-Arylpropynamides with N-Sulfanylsuccinimides: Divergent Synthesis of 3-Sulfenyl Quinolin-2-ones and Azaspiro[4,5]trienones

Switchable ortho/ipso-cyclization of N-arylpropynamides induced with N-sulfanylsuccinirnides as general sulfur reagents is reported. In the presence of MeOH, parafluoro N-arylpropynamides exclusively undergo the ipso-cyclization to give 3-sulfenyl azaspiro[4,5]trienones. Two kinds of bioactive heterocycles, benzothieno-[3,2-b]quinoline and 42,3-dquinolone, have been directly and efficiently prepared from the corresponding sulfenylated products.