Highly functionalized benzazepines have been synthesized by using various substituted indoles and dialkylacetylene dicarboxylates under thermal and open air conditions. The reaction was carried out in a solvent and under catalyst free conditions and the products are formed in very good yields. The reaction proceeds in a concerted fashion thus providing potentially bioactive benzazepines by ring expansion of a five-membered indole ring. It is also described that the ring contraction of seven-membered benzazepines in the presence of KO^tBu base at room temperature smoothly afforded the corresponding 3-alkenylated indole derivatives in very good yields.