Abstract A series of 2‐ and 3‐indolylthioalkanoic acids of various chain lengths were cyclized under dehydrative conditions affording tricyclic indole‐containing ring systems wherein the third ring contains a sulfur atom attached to the 2‐ or 3‐position of the indole ring. This methodology affords entry into the novel thiepino[3,2‐b]indole, thiocino[2,3‐b]indole and thiocino[3,2‐b]indole ring systems.