[4 + 2] Benzannulation of 3‑Alkenylpyrroles/Thiophenes with Propargylic Alcohols: Access to Substituted Indoles, Benzothiophenes, and Aza[5]helicenes

An efficient and practical one-pot [4 + 2] benzannulation method to produce highly substituted indoles and 1-benzothiophenes via sequential acid-catalyzed propargylation/base-mediated cycloisomerization reactions has been developed. This method allows access to differently substituted (mainly on phenyl ring) indoles and 1-benzothiophenes from the reaction of 3-alkenylpyrroles/-thiophenes as C4 synthons with 1-aryl/1-heteroaryl propargylic alcohols as C2 synthons. Interestingly, dialkynyl substrates can undergo tandem benzannulations to give substituted aza[5]­helicenes in 82–83% yield.