Abstract A detailed examination of the synthesis of functionalized 6,11‐dihydro‐5 H ‐benzo[ b ]pyrimido[5,4‐ f ]azepines 4 is described. Base‐promoted aromatic nucleophilic substitution of 5‐allyl‐4,6‐dichloropyrimidines 1a – c with different N ‐substituted anilines and indoline gave the corresponding aminolysis products 3a – p , which on acid‐promoted intramolecular Friedel–Crafts cyclization produced the target polysubstituted 6,11‐dihydro‐5 H ‐benzo[ b ]pyrimido[5,4‐ f ]azepines 4a – p in moderate to very high yields.