Synthesis of Pyrimidine‐Fused Benzazepines from 5‐Allyl‐4,6‐dichloropyrimidines

Abstract

AbstractA detailed examination of the synthesis of functionalized 6,11‐dihydro‐5H‐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‐5H‐benzo[b]pyrimido[5,4‐f]azepines 4a–p in moderate to very high yields.