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

A 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 prod...

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Veröffentlicht in:European journal of organic chemistry 2015-08, Vol.2015 (24), p.5360-5369
Hauptverfasser: Acosta-Quintero, Lina M., Jurado, Jorge, Nogueras, Manuel, Palma, Alirio, Cobo, Justo
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Sprache:eng
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Zusammenfassung:A 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. An efficient two‐step protocol to access a new series of polysubstituted 6,11‐dihydro‐5H‐benzo[b]pyrimido[5,4‐f]azepines from readily available 5‐allyl‐4,6‐dichloropyrimidines is described for the first time.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500632